Abstract
The first review on the origin and chemistry of naturally-occurring isocyanides by Edenborough and Herbert (1) appeared in 1988. In this review the isocyanides, more commonly named as isonitriles (RNC), were divided into non-marine and marine groups. The non-marine isocyanides were divided into xanthocillin-type or cyclopentyltype isocyanides. A few others which did not fit into either category were placed in a miscellaneous section. All isocyanides of marine origin, which had been isolated from sponges and their predators, were sesquiterpenes and diterpenes.
At the time when the isocyanokalihinols and hapalindoles were discovered, the author was at the University of Hawaii on leave. This review is dedicated to Professor Paul J. Scheuer and Richard E. Moore on the occasions of their 86th and 67th birthdays respectively.
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References
Edenborough MS, Herbert RB (1988) Naturally Occurring Isocyanides. Nat Prod Rep 5: 229
Cafieri F, Fattorusso E, Magno S, Santacroce C, Sica D (1973) Isolation and Structure of Axisonitrile-1 and Axisothiocyanate-l. Two Unusual Scsquiterpenoids from the Marine Sponge Axinella cannabina. Tetrahedron 29: 4259
Minale L, Riccio R, Sodano G (1974) Acanthellin-1, an Unique Sesquiterpene Isonitrile from the Sponge Acanthella acuta. Tetrahedron 30: 1341
Burreson BJ, Scheuer PJ (1974) Isolation of a Diterpenoid Isonitrile from a Marine Sponge. J Chem Soc, Chem Commun 1035
Moore RE, Cheuk C. Yang X-QG, Patterson GML, Bonjouklian R, Smitka TA, Mynderse JS, Foster RS, Jones ND, Swartzendruber JK, Deeter JB (1987) Hapalindoles, Antibacterial and Antimycotic Alkaloids from the Cyanophyte Hapalosiphon fontinalis. J Org Chem 52: 1036
Moore RE, Yang X-QG, Patterson GML (1987) Fontonamide and Anhydrohapaloxindole A, Two New Alkaloids from the Blue-Green Alga Hapalosiphon fontinalis. J Org Chem 52: 3773
Chang CWJ, Patra A, Baker JA, Scheuer PJ (1987) Kalihinols, Multifunctional Diterpenoid Antibiotics from Marine Sponges Acanthella spp. J Am Chem Soc 109: 6119
Moore RE, Cheuk C, Patterson GML (1984) Hapalindoles: New Alkaloids from the Blue-Green Alga Hapalosiphon fontinalis. J Am Chem Soc 106: 6456
Chang CWJ, Patra A, Roll DM, Scheuer PJ, Matsumoto GK, Clardy J (1984) Kalihinol A, a Highly Functionalized Diisocyano Diterpenoid Antibiotic from a Sponge. J Am Chem Soc 106: 4644
Patra A, Chang CWJ, Scheuer PJ, Van Duync GD, Matsumoto GK, Clardy J (1984) An Unprecedented Triisocyano Diterpenoid Antibiotic from a Sponge. J Am Chem Soc 106: 7981
Hagedorn I, Tönjes H (1956) Clarification of Constitution of Xanthocillin, an Antibiotic. Brief Communication. Pharmazie 11: 409 [Chem Abstr (1957) 50: 17161i]
Hagedorn I, Tönjes H (1957) Konstitutionsaufklärung von Xanthocillin, einem Neuen Antibiotikum. Pharmazie 12: 567 [Chem Abstr (1958) 52: 6362c]
Rothe W (1950) New Antibiotic. Pharmazie 5: 190 [Chem Abstr (1950) 44: 8063e]
Pyke TR, Dietz A (1966) U-21,963, A New Antibiotic. I. Discovery and Biological Activity. Appl Microbiol 14: 506
Meyer CE (1966) U-21,963, A New Antibiotic. II. Isolation and Characterization. Appl Microbiol 14: 51 I
Coats JH, Meyer CE, Pyke TR (1971) Antibiotic Dermadin. U.S. Patent 3,627, 882
Hofmann AW (1874) Synthese des Ätherischen Ois der Cochlearia officinales. Ber Dtsch Chem Ges 7: 508
Kjer A (1960) Naturally Derived isoThiocyanates (Mustard Oils) and their Parent Glucosides. Fortschr Chem Org Naturstoffe 18: 122
Larsen PO (1981) Glucosinolatcs. In: Conn EE (ed) The Biochemistry of Plants, a Comprehensive Treatise, vol 7. Academic Press, New York, pp 501–525
Zhang Y, Talalay P. Cho C-G, Posner GH (1992) A Major Inducer of Anticarcinogenic Protective Enzymes from Broccoli: Isolation and Elucidation of Structure. Proc Natl Acad Sci USA 89: 2399
Zhang Y, Kensler TW, Cho C-G, Posner GH, Talalay P (1994) Anticarcinogenic Activities of Sulforaphane and Structurally Related Synthetic Norbornyl Isothiocyanates. Proc Natl Acad Sci USA 91: 3147
Fahey JW, Zhang Y, Talalay P (1997) Broccoli Sprouts: An Exceptionally Rich Source of Inducers of Enzymes that protect against Chemical Carcinogens. Proc Natl Acad Sci USA 94: 10367
Ugi I (ed) (1971) Isonitrile chemistry. Academic Press, New York
Itoh J, Takeuchi Y, Gomi S, Inouye S, Mikawa T, Yoshikawa N, Ohkishi H (1990) MK 4588, a New Antibiotic Related to Xanthocillin, from Leptosphaeria sp L-179. J Antibiot 43: 456
Lee C, Koshino H, Chung M, Lee H, Koshino H, Kho Y (1996) New Melanin Synthesis Inhibitors Produced by Trichoderrna harzianum. Abstr P7. 37th Annual Meeting, Amer Soc Pharmacognosy, Santa Cruz
Minale L (1978) Terpenoids from Marine Sponges. In: Scheuer PJ (ed) Marine Natural Products. Chemical and Biological Perspective, vol 2. Academic Press, New York, pp 175–239
Minale L, Cimino G, De Stefano S, Sodano G (1976) Natural Products from Porifera. Prog Chem Org Nat Prod 33: 1
Faulkner DJ (1977) Interesting Aspects of Marine Natural Products Chemistry. Tetrahedron 33: 1421
Faulkner DJ (1984) Marine Natural Products: Metabolites of Marine Invertebrates. Nat Prod Rep 1: 551
Faulkner DJ (1986) Marine Natural Products. Nat Prod Rep 3: 551
Faulkner DJ (1987) Marine Natural Products. Nat Prod Rep 4: 539
Faulkner DJ (1988) Marine Natural Products. Nat Prod Rep 5: 613
Faulkner DJ (1990) Marine Natural Products. Nat Prod Rep 7: 269
Faulkner DJ (1991) Marine Natural Products. Nat Prod Rep 8: 97
Faulkner DJ (1992) Marine Natural Products. Nat Prod Rep 9: 323
Faulkner DJ (1993) Marine Natural Products. Nat Prod Rep 10: 497
Faulkner DJ (1994) Marine Natural Products. Nat Prod Rep 11: 355
Faulkner DJ (1995) Marine Natural Products. Nat Prod Rep 12: 223
Faulkner DJ (1996) Marine Natural Products. Nat Prod Rep 13: 75
Faulkner DJ (1997) Marine Natural Products. Nat Prod Rep 14: 259
Faulkner DJ (1998) Marine Natural Products. Nat Prod Rep 15: 113
Faulkner DJ (1999) Marine Natural Products. Nat Prod Rep 16: 155
Scheuer P (1992) Isocyanides and Cyanides as Natural Products. Acc Chem Res 25: 433
Chang CWJ, Scheuer PJ (1993) Marine Isocyano Compounds. In: Scheuer PJ (ed) Topics in Current Chemistry: Marine Natural Products - Diversity and Biosynthesis, vol 167. Springer, Berlin Heidelberg New York, pp 33–75
Raven PH, Evert RR, Curtis H (1976) Biology of Plants. Worth, New York
Fay P (1983) The Blue Greens In: The Institute of Biology. Studies in Biology No. 160. Edward Arnold, Australia
Park A, Moore RE, Patterson GML (1992) Fischerindole L, a New lsonitrile from the Terrestrial Blue-Green Alga Fischerella musciola. Tetrahedron Lett 33: 3257
Carmeli S, Moore RE, Patterson GML, Mori Y, Suzuki M (1990) Isonitriles from the Blue-Green Alga Scvtonema mirabile. J Org Chem 55: 4431
Bergquist PR (1978) Sponges, University of California Press, Berkeley
Bergquist PR, Wells RJ (1983) Chemotaxonomy of the Porifera: The Development and Current Status of the Field. In: Scheuer PJ (ed) Marine Natural Products. Chemical and Biological Perspective, vol 5. Academic Press, New York, pp 1–50
Braekman J-C, Daloze D, Stoller C, Van Soest RWM (1992) Chemotaxonomy of Agelas (Porifera: Demospongiae). Biochem Systematics & Ecol 20: 417
Rodríguez J, Nieto RM, Hunter LM, Diaz MC, Crews P (1994) Variation Among Known Kalihinol and New Kalihinene Diterpenes from the Sponge Acanthella cavernosa. Tetrahedron 50: 11079
Burreson BJ, Scheuer PJ, Finer J. Clardy J (1975) 9-Isocyanopupukeanane, a Marine Invertebrate Allomone with a New Sesquiterpene Skeleton. J Am Chem Soc 97: 4763
Cimino G, De Rosa S, De Stefano S, Sodano G (1982) The Chemical Defense of Four Mediterranean Nudibranchs. Comp Biochem Physiol 73B: 471
Thompson JE, Walker RP, Wratten SJ, Faulkner DJ (1982) A Chemical Defense Mechanism for the Nudibranch Cadlina luteomarginatu. Tetrahedron 38: 1865
Karuso P (1987) Chemical Ecology of Nudibranchs. In: Scheuer PJ (ed) Bioorganic Marine Chemistry. Springer-Verlag, Berlin, pp 31–60
Fattorusso E, Magno S, Mayol L, Santacroce C, Sica D (1975) New Sesquiterpenoids from the Sponge Axinella cannahina. Tetrahedron 31: 269
Tada H, Tozyo T, Shiro M (1988) A New Isocyanide from a Sponge. Is the Formamide a Natural Product? J Org Chem 53: 3366
Gulavita NK, De Silva ED, Hagadone MR, Karuso P, Scheuer PJ (1986) Nitrogenous Bisabolene Sesquiterpenes from Marine Invertebrates. J Org Chem 51: 5136
He H-Y, Faulkner DJ, Shumsky JS, Hong K, Clardy J (1989) A Sesquiterpene Thiocyanate and Three Sesquiterpene Isothiocyanates from the Sponge Tracln’opsis uplvsinoides. J Org Chem 54: 2511
Virtanen AI, Saarivirta M (1962) Formation of Benzyl Cyanide, Benzyl Isothiocyanate, and Benzyl Thiocyanate in the Crushed Seeds of Lepidium sativuv. Suomen Kemistilehti 35B: 248 [Chem Abstr (1963) 58: 7136e]
Saarivirta M (1973) Formation of Benzyl Cyanide, Benzyl Thiocyanate, Benzyl Isothiocyanate and Benzyl Amine from Benzyl Glucosinolate in Lepidiwn. Planta Medica 24: 112
Hegnauer R, Hegnauer M (1992) Chemotaxonomie der Planzen. General Register, vol 10. Birkhaeuser, Basel
Sullivan BW, Faulkner DJ, Okamoto KT, Chen MHM, Clardy J (1986) (6R,7S)-7Amino,7,8-dihydro-x-bisabolene, an Antimicrobial Metabolite from the Marine Sponge Halicliondria sp. J Org Chem 51: 5134
Chemical Abstracts, Index Guide (1994) Chemical Abstracts Service, Columbus, Ohio
Moss GP, Smith PAS, Tavernier D (1995) Glossary of Class Names of Organic Compounds and Reactive Intermediates Based on Structure. Pure Appl Chem 67: 1307
International Union of Pure and Applied Chemistry: Nomenclature of Organic Chemistry, Section C. (1965), Butterworths, London
Stratmann K, Moore RE, Bonjouklian R, Dcetcr JB, Patterson GML, Shaffer S, Smith CD, Smitka TA (1994) Welwitindolinones, Unusual Alkaloids from the Blue-Green Algae Hapalosiphon mehritschii and Westiclla intricata. Relationship to Fischerindolcs and Hapalindoles. J Am Chem Soc 116: 9935
Klein D, Dalozc D, Braekman JC, Hoffmann L, Demoulin V (1995) New Hapalindoles from the Cyanophytc Hapulosiphon laingii. J Nat Prod 58: 1781
Bonjouklian R, Moore RE, Patterson GML (1988) Acid-Catalyzed Reactions of Hapalindoles. J Org Chem 53: 5866
Karuso P, Hagadonc MR, Scheuer PJ, Bergquist PR (1990) Chemotaxonomy of the Porifera by Infrared Spectroscopy. In: Rützler K (ed) New Perspectives in Sponge Biology. Smithsonian Institution, Washington, DC, pp 55–60
Ashworth MRF (1972) The Determination of Sulphur-containing Groups, Academic Press, London
Lim YY, Stein AR (1971) Acid-catalyzed Solvolysis of Isonitriles, I. Can Chem 49: 2455
Giles DE (1977) Kinetics and Mechanisms of Reaction of Cyanates and Related Compounds. In: Patai S (ed) The Chemistry of Cyanates and their Derivatives. Part I. John Wiley & Sons. New York
Satchel] DPN, Satchell RS (1975) Acylation by Ketens and Isocyanates. A Mechanistic Comparison. Chem Soc Reviews 4: 23
Pretsch E, Clerc T, Seibl J, Simon W (1989) Spectral Data for Structure Determination of Organic Compounds, 2nd edn. Springer-Verlag, Berlin Heidelberg New York
Kuntz Jr ID, von Schleyer PR, Allerhand A (1961) N14H’ Nuclear Resonance Coupling in Isonitriles. J Chem Phys 35: 1533
König GM, Wright AD (1995) 1H (300 MHz) and 13C NMR Spectral Assignments for Diisocyanoadociane. Magn Reson Chem 33: 694
Crews P, Rodríguez J, Jaspars M (1998) Organic Structure Analysis. Oxford, New York
Saxton JE (1995) Recent Progress in the Chemistry of the Monoterpenoid Indole Alkaloids. Nat Prod Rep 12: 385
Moore RE, Patterson GML (1985) Hapalindoles. Eur Patent O 171 283 A2
Schwartz RE, Hirsch CF, Sesin DF, Flor JE, Chartrain M, Fromtling RE, Harris GH, Salvatore MJ, Liesch JM, Yudin K (1990) Pharmaceuticals from Cultured Algae. J Indust Microbiol 5: 113
Moore RE, Yang XQG, Patterson GML, Bonjouklian R, Smitka TA (1989) Hapalonamides and other Oxidized Hapalindoles from Hapalosiphon fontinalis. Phytochemistry 28: 1565
Schwartz RE, Hirsch CF, Springer JP, Pettibone DJ, Zink DL (1987) Unusual Cyclopropane-containing Hapalindolinones from a Cultured Cyanobacterium. J Org Chem 52: 3704
Jimenez JI, Husebo TL, Jensen CM, Patterson GML, Moore RE (1999) Personal communication.
Jimenez J, Huber U, Moore RE, Patterson GML (1999) Oxidized Welwitindolinones from Terrestrial Fischerella spp. J Nat Prod 62: 569; ibid 62: 940
Smitka TA, Bonjouklian R, Doolin L, Jones ND, Deeter JB, Yoshida WY, Prinsep MR, Moore RE, Patterson GML (1992) Ambiguine Isonitriles, Fungicidal Hapalindole-Type Alkaloids from Three Genera of Blue-Green Algae Belonging to the Stigonemataceae. J Org Chem 57: 857
Huber U, Moore RE, Patterson GML (1998) Isolation of a Nitrile-Containing Indole Alkaloid from the Terrestrial Blue-Green Algae Hapalosiphon delicatulus. J Nat Prod 61: 1304
Bonjouklian R, Spangle LA, Moore RE (1989) Facile Intramolecular Photoaddition and Oxidative Dimerization of Hapalindole E, a Naturally Occurring IsonitrileContaining Indole. J Org Chem 54: 719
Murataki H, Natsume M (1989) Total Synthesis of Marine Alkaloids (±)Hapalindoles J and M. Tetrahedron Lett 30: 1815
Murataki H, Natsume M (1990) Synthetic Studies of Marine Alkaloids Hapalindoles. Part 1. Total Synthesis of (±)-Hapalindoles J and M. Tetrahedron 46: 6331
Murataki H, Natsume M (1990) Synthetic Studies of Marine Alkaloids Hapalindoles. Part 2. Lithium Aluminum Hydride Reduction of the Electron-Rich CarbonCarbon Double Bond Conjugated with the Indole Nucleus. Tetrahedron 46: 6343
Murataki H, Kumagami H, Natsume M (1990) Synthetic Studies of Marine Alkaloids Hapalindoles. Part 3. Total Synthesis of (±)-Hapalindoles H and U. Tetrahedron 46: 6351
Vaillancourt V, Albizati KF (1993) Synthesis and Absolute Configuration of (+)-Hapalindole Q. J Am Chem Soc 115: 3499
Fukuyama T, Chen X (1994) Stereocontrolled Synthesis of ()-Hapalindole G. J Am Chem Soc 116: 3125
Sakagami M, Muratake H, Natsume M (1994) Preparation of Alkyl-Substituted Indoles in the Benzene Portion. Part 12. Enantiospecific Synthesis of Hapalindole O. Chem Pharm Bull 42: 1393
Burreson BJ, Christophersen C. Scheuer PJ (1975) Co-occurrence of Two Terpenoid Isocyanide Formamide Pair in a Marine Sponge (Halichondria sp). Tetrahedron 31: 2015
Wiemer DF, Meinwald J, Prestwich GD, Solheim BA, Clardy J (1980) Biflora-4,10 (19),15-triene: A New Diterpene from a Termite Soldier (Isoptera Termitidae Termitinae). J Org Chem 45: 191
Ishitsuka MO, Kusumi T. Ichikawa A, Kakisawa 1–1 (1990) Bicyclic Diterpenes from Two Species of Brown Algae of the Dictyotaceae. Phytochemistry 29: 2605
Hooper JNA, Levi C (1993) Axincllida from the New Caledonian Lagoon. Invertebr Taxon 7: 1395
The presence of isocyano-scsquiterpencs and -diterpenes in sponges from the genus Acanthella is uncommon; however, cf. ref. 107.
Omar S, Albert C, Fanni T, Crews P (1988) Polyfunctional Diterpene Isonitriles from Marine Sponge Acanthella cavernosa. J Org Chem 53: 5971
Fusetani N, Yasumuro K, Kawai H, Natori T, Brinen L, Clardy J (1990) Kalihinene and Isokalihinol B, Cytotoxic Diterpene Isonitriles from the Marine Sponge Acanthella klethra. Tetrahedron Lett 31: 3599
Alvi KA, Tenenbaum L, Crews P (1991) Anthelmintic Polyfunctional Nitrogen-containing Terpenoids from Marine Sponges. J Nat Prod 54: 71
Trimurtulu G, Faulkner DJ (1994) Six New Diterpene Isonitriles from the Sponge Acanthella cavernosa..I Nat Prod 57: 501
Braekman JC, Daloze D, Gregoire F, Popov S, Van Soest R (1994) Two New Kalihinenes from the Marine Sponge Acanthella cavernosa. Bull Soc Chim Belg 103: 187
Hirota H, Tomono Y, Fusetani N (1996) Terpenoids with Antifouling Activity against Barnacle Larvae from the Marine Sponge Acanthella cavernosa. Tetrahedron 52: 2359
Okino T, Yoshimura E, Hirota H, Fusetani N (1995) Antifouling Kalihinenes from the Marine Sponge Acanthella cavernosa. Tetrahedron Lett 36: 8637
Okino T, Yoshimura E. Hirota H, Fusetani N (1996) New Antifouling Kalihipyrans from the Marine Sponge Acanthella cavernosa. J Nat Prod 59: 1081
Wolf D, Schmitz FJ (1998) New Diterpene Isonitriles from the Sponge Phakellia pulcherrima. J Nat Prod 61: 1524
Miyaoka H. Shimomura M, Kimura H, Yamada Y, Kim H-S, Wataya Y (1998) Antimalarial Activity of Kalihinol A and New Relative Diterpenoids from the Okinawan Sponge, Acanthella sp. Tetrahedron 54: 13467.
Wratten SJ., Faulkner DJ, Hirotsu K, Clardy J (1978) Diterpenoid Isocyanides from the Marine Sponge Hvmeniacidon amphilecta. Tetrahedron Lett 4345
Kazlauskas R, Murphy PT., Wells RJ, Blount JF (1980) New Diterpene Isocyanides from a Sponge. Tetrahedron Lett 21: 315
Baker JT, Wells RJ., Oberhänsli WE., Hawes GB (1976) A New Diisocyanide of Novel Ring Structure From a Sponge. J Am Chem Soc 98: 4010
Garson MJ (1986) Biosynthesis of the Novel Diterpene Isonitrile Diisocyanoadociane by a Marine Sponge of the Amphimedon Genus: Incorporation Studies with Sodium [14C]Cyanide and Sodium [2–14C]Acetate. J Chem Soc, Chem Commun 35
Fookes CJR, Garson MJ, Macleod JK, Skelton BW, White AH (1988) Biosynthesis of Diisocyanoadociane, a Novel Diterpene from the Marine Sponge Amphimedon sp. Crystal Structure of a Monoamide Derivative. J Chem Soc, Perkin Trans 11003
König GM, Wright AD, Angerhofer CK (1996) Novel Potent Antimalarial Diterpene Isocyanates, Isothiocyanates, and Isonitriles from the Tropical Marine Sponge Cymbastela hooperi J Org Chem 61: 3259
Angerhofer CK, König GM, Wright AD, Sticher O, Milhous WK, Cordell GA, Farnsworth NR, Pezzuto JM (1992) Selective Screening of Natural Products: Resource for the Discovery of Novel Antimalarial Compounds. In: Atta-ur-Rahman (ed) Advances in Natural Product Chemistry, Harwood Academic Publishers, pp 311–329
Linden A, König GM, Wright AD (1996) Four Diterpene Isonitriles from the Sponge Cymbastela hooperi. Acta Crystallogr, Sect C, 52: 2607
Wright AD, König GM, Angerhofer CK, Greenidge P, Linden A, DesqueyrouxFaúndez R (1996) Antimalarial Activity: The Search for Marine-derived Natural Products with Selective Antimalarial Activity. J Nat Prod 59: 710
Molinski TF, Faulkner DJ, van Duyne GD, Clardy J (1987) Three New Diterpene Isonitriles from a Palauan Sponge of the Genus Halichondria. J Org Chem 52: 3334
Sharma HA, Tanaka JL, Higa T, Lithgow A, Bernardinelli G, Jefford CW (1992) Two New Diterpene Isocyanides from a Sponge of the Family Adocidae. Tetrahedron Lett 33: 1593
Ichikawa Y, Yamazaki M, Isobe M (1993) Novel, Regioselective Allylamine Construction; First Synthesis of Geranyllinaloisocyanide, a Diterpene from the Marine Sponge, Halichondria sp. J Chem Soc, Perkin Trans I 2429
Corey EJ, Magriotis PA (1987) Total Synthesis and Absolute Configuration of 7,20Diisocyanoadociane. J Am Chem Soc 109: 287
Piers E, Llinas-Brunet M (1989) Total Synthesis of (f)-8,15-Diisocyano-11(20)amphilectenc. J Org Chem 54: 1483
Piers E, Llinas-Brunet M, Oballa RM (1993) Total Synthesis of Amphilectane-type Diterpenoids: (±)-8,15-Diisocyano-11(20)-amphilectene. Can J Chem 71: 1484
Piers E, Romero MA (1993) Total Synthesis of Amphilectane-type Diterpenoids: (f)-8-Isocyano-10,14-amphilectadiene. Tetrahedron 49: 5791
Johannes RE (1963) A Poison-Secreting Nudibranch (Mollusca: Opisthobranch). Veliger 5: 104
Hagadone MR, Burreson BJ, Scheuer PJ, Finer JS, Clardy J (1979) Defense Allomones of the Nudibranch Phyllidia varicosa Lamarck 1801. HeIv Chim Acta 62: 2484
Pawlik JR (1993) Marine Invertebrate Chemical Defenses. Chem Rev 93: 1771
Cimino G, De Rosa S, De Stefano S, Sodano G, Villani G (1983) Dorid Nudibranch Elaborates its Own Chemical Defense. Science 219: 1237
Fusetani N, Wolstenholme HJ, Matsunaga S, Hirota H (1991) Two New Sesquiterpene Isonitriles from the Nudibranch, Phyllidia pustulosa. Tetrahedron Lett 32: 7291
Fusetani N, Wolstenholme HJ, Shinoda K, Asai N, Matsunaga S (1992) Two Sesquiterpene Isocyanides and a Sesquiterpene Thiocyanate from the Marine Sponge Acanthella cf. cavernosa and the Nudibranch, Phyllidia ocellata. Tetrahedron Lett 33: 6823
Burgoyne DL, Dumdei EJ, Andersen RJ (1993) Acanthenes A to C: A Chloro, Isothiocyanate, Formamide Sesquiterpene Triad Isolated From The Northeastern Pacific Marine Sponge Acanthella sp. and the Dorid Nudibranch Cadlina luteomarginata. Tetrahedron 49: 4503
Okino T, Yoshimura E, Hirota H, Fusetani N (1996) New Antifouling Sesquiterpenes from Four Nudibranchs of the Family Phyllidiidae. Tetrahedron 52: 9447
Fusetani N, Hiroto H, Okino T, Tomono Y, Yoshimura Y (1996) Antifouling Activity of Isocyanoterpenoids and Related Compounds Isolated from a Marine Sponge and Nudibranchs. J Nat Toxins 5: 249
Di Blasio B, Fattorusso E, Magno S, Mayol L, Pedone C, Santacroce C, Sica D (1976) Axisonitrile-3, Axisothiocyanate-3 and Axamide-3. Sesquiterpenes with a Novel Spiro[4,5]decane Skeleton from the Sponge Axinella cannabina. Tetrahedron 32: 473
Gusen HJM, Wijnberg JBPA, de Groot A (1995) Structure, Occurrence, Biosynthesis, Biological Activity, Synthesis, and Chemistry of Aromadendrane Sesquiterpenoids. Prog Chem Org Nat Prod 64: 149
Fattorusso E, Magno S, Mayol L, Santacroce C, Sica D (1974) Isolation and Structure of Axisonitrile-2. A New Sesquiterpenoid Isonitrile from the Sponge Axinella cannabina. Tetrahedron 30: 3911
Ciminiello P, Fattorusso E, Magno S, Mayol L (1984) New Nitrogenous Sesquiterpenes from the Marine Sponge Axinella cannabina. J Org Chem 49: 3949
Ciminiello P, Fattorusso E, Magno S, Mayol L (1985) Sesquiterpenoids based on the Epi-Maaliane Skeleton From the Marine Sponge Axinella cannabina. J Nat Prod 48: 64
Ciminiello P, Fattorusso E, Magno S, Mayol L (1987) New Nitrogenous Sesquiterpenes based on Alloaromadendrane and epi-eudesmane Skeletons from the Marine Sponge Axinella cannabina. Can J Chen 65: 518
Iengo A, Mayol L, Santacroce C (1977) Minor Sesquiterpenoids from the Sponge Axinella cannabina. Experientia 33: 11
Adinolfi M, De Napoli L, Di Blasio B, Iengo A, Pedone C, Santacroce C (1977) The Absolute Configuration of the Axane Sesquiterpenes from the Sponge Axinella cannabina. Tetrahedron Lett 2815.
Piers E, Ycung BWA (1986) Total Synthesis of the Sesquiterpenoids (f)-Axamide-1, (f)-Axisonitrile-1, and the Corresponding C-10 Epimers. Can J Chem 64: 2475
Tada H, Yasuda F (1985) Metabolites from the Marine Sponge Epipolasis kushimotoensis. Chem Pharm Bull 33: 1941
Da Silva CC, Almagro V, Marsaioli AJ (1993) Direct Route to Terpene Isothiocyanates. Tetrahedron Lett 34: 6717
Da Silva CC, Almagro V, Zukerman-Schpector J, Castellano EE, Marsaioli AJ (1994) An Easy Route to (-)-10(R)-Isothiocyanoaromadendrane and (-)-10(S)lsothiocyanoallo-aromadendrane. J Org Chem 59: 2880
Braekman JC, Daloze D., Deneubourg F., Huysecom J, Vandevyver G (1987) 1-isocyano-aromadendrane, a New Isonitrile Sesquiterpene from the Sponge Acanthella acuta. Bull Soc Chim Belge 96: 539
Brockman J-C., Daloze D, Stoller C, Dccicrcq J-P (1989) The Configuration of Palustrol and Related Compounds. Bull Soc Chim Belge 98: 869
Braekman JC, Daloze D, Moussiaux B, Stoller C, Deneubourg F (1989) Sponge Secondary Metabolites: New Results. Pure Appl Chem 61: 509
Mayol L, Piccialli V. Sica D (1987) Nitrogenous Sesquiterpenes from the Marine Sponge Acanthella acula: Three New IsocyanideIsothiocyanate Pairs. Tetrahedron 43: 5381
Capon RJ, Macleod JK (1988) New Isothiocyanate Sesquiterpenes from the Australian Marine Sponge Acanthella pulcherrima. Aus J Chem 41: 979
Kassuhlke KE, Potts BCM, Faulkner DJ (1991) New Nitrogenous Sesquiterpenes from Two Phillipine Nudibranchs, Phyllidia pustulosa and P. varicosa, and from a Palauan Sponge, Halichondria cf. Halichondria cf. lendenfeldi. J Org Chem 56: 3747
He H-Y, Salvá J, Catalos RF, Faulkner DJ (1992) Sesquiterpene Thiocyanates and Isothiocyanates from Axinyssa aplysinoides. J Org Chem 57: 3191
Ciminiello PS, Magno S, Mayol L, Piccialli V (1987) Cis-eudesmane Nitrogenous Metabolites from the Marine Sponges Axinella cannabina and Acanthella acuta. J Nat Prod 50: 217
König GM, Wright AD, Sticher O, Fronczek FR (1992) Two New Sesquiterpene Isothiocyanates from the Marine Sponge Acanthella klethra. J Nat Prod 55: 633
Pais M, Fontaine C, Laurent D, La Barre S, Guittet E (1987) Stylotelline, A New Sesquiterpene Isocyanide from the Sponge Stylotella sp. Application of 2D-NMR in Structure Determination. Tetrahedron Lett 28: 1409
Dumdei EJ, Flowers AE, Garson MJ, Moore CJ (1997) The Biosynthesis of Sesquiterpene Isocyanides and Isothiocyanates in the Marine Sponge Acanthella cavernosa (Dendy); Evidence for Dietary Transfer to the Dorid Nudibranch Phyllidiella pustulosa. Comp Biochem Physiol 118A: 1385
Angerhofer CK, Pezzuto JM, König GM, Wright AD, Sticher O (1992) Antimalarial Activity of Sesquiterpenes from the Marine Sponge Acanthella klethra. J Nat Prod 55: 1787
Burreson BJ, Christophersen C, Scheuer PJ (1975) Cooccurrence of a Terpenoid IsocyanideFormamide Pair in the Marine Sponge Halichondria sp. J Am Chem Soc 97: 201
Marcus AH, Molinski TF, Fahy E, Faulkner DJ, Xu C, Clardy J (1989) 5-Isothiocyanatopupukeanane from a Sponge of the Genus Axinyssa. J Org Chem 54: 5184
Compagnone RS, Faulkner DJ (1995) Metabolites of the Palauan Sponge Axinyssa Aplysinoides. J Nat Prod 58: 145
Ciminiello P, Fattorusso E, Magno S, Mayol L (1986) Minor Nitrogenous Sesquiterpenes from the Marine Sponge Axinella cannabina. A Hypothesis for the Biogenesis of the Spiro-axane Skeleton. Experientia 42: 625
Nakamura H, Deng S, Takamatsu M, Kobayashi J, Ohizumi Y, Hirata Y (1991) Structure of Halipanicine, a New Sesquiterpene Isothiocyanate from the Okinawan Marine Sponge Halichondria panicea (Pallas). Agrie Biol Chem 55: 581
Simpson JS, Garson MJ, Hooper JNA, Cine EI, Angerhofer CK (1997) Terpene Metabolites from the Tropical Marine Sponge Axinyssa sp. nov. Aus J Chem 50: 1123
Li C-J, Schmitz FJ, Kelly-Borges M (1998) A New Lysine Derivative and New 3-Bromopyrrole Carboxylic Acid Derivative from Two Marine Sponges. J Nat Prod 61: 387
Hirota H, Okino T, Yoshimura E, Fusetani N (1998) Five New Antifouling Sesquiterpenes from Two Marine Sponges of the Genus Axinyssa and the Nudibranch Phyllidia pustulosa. Tetrahedron 54: 13971
Ohta Y, Ohara K, Hirose Y (1968) Acid-catalyzed Isomerization of a-Cubebene, a-Copaene, and a-Ylangene. Tetrahedron Lett 4181
Nakamura H, Kobayashi J, Ohizumi Y, Hirata Y (1984) Novel Bisabolene-type Sesquiterpenoids with a Conjugated Diene Isolated from the Okinawan Sea Sponge Theonella cf swinhoei. Tetrahedron Lett 25: 5401
Li CJ, Schmitz FJ (1999) New Nitrogenous Bisabolene-Type Sesquiterpenes from a Micronesian Marine Sponge Axinyssa sp. J. Nat Prod 62: 1330
Nishizawa M, Inoue A, Hayashi Y, Sastrapradja S, Kosela S, Iwashita T (1984) Structure of Aphanamol I and II. J Org Chem 49: 3660
Fusetani N, Wolstenholme HJ, Matsunaga S (1990) Co-occurrence of 9-Isocyanopupukeanane and its C-9 Epimer in the Nudibranch Phyllidia bourguini. Tetrahedron Lett 31: 5623
Karuso P, Poiner A, Scheuer PJ (1989) Isocyanoneopupukeanane, a New Tricyclic Sesquiterpene from a Sponge. J Org Chem 54: 2095
Pham AT, Ichiba T, Yoshida WY, Scheuer PJ, Uchida T, Tanaka J-I, Higa T (1991) Two Marine Sesquiterpene Thiocyanates. Tetrahedron Lett 32: 4843
Patil AD, Freyer Ai, Rcichweiss R, Bear MF, Faucett L, Johnson RK, Haltiwanger RC, Eggleston DS (1997) Two New Nitrogenous Sesquiterpenes from the Sponge Axinyssa aplysinoides. J Nat Prod 60: 507
Corey EJ, Behforouz M, Ishiguro M (1979) Total Synthesis of the Racemate of the Sesquiterpenoid Marine Allomone 9-Isocyanopupukeanane. J Am Chem Soc 101: 1608
Yamamoto H, Sham HL (1979) Total Synthesis of (f)-9-Isocyanopupukeanane. J Am Chem Soc 101: 1609
Piers E, Yeung BWA, Rettig SJ (1987) Methylenecyclohexane Annulation. Total Synthesis of (t)-Axamide-1, (f)-Axisonitrile-1, and the Corresponding C-10 Epimers. Tetrahedron 43: 5521
Guével A-C, Hart DJ (1994) A Concise Stereoselective Synthesis of the Axane-1 Family of Sesquiterpenoids Using an Intramolecular Michael Addition. Synlett 169
Hart DJ. Lai C-S (1989) Total Synthesis of the Axane-4 Family of Sesquiterpenoids Using a Stereoselective Intramolecular Conjugate Addition. Synlett 49
Chenera B, Chuang C-P, Hart DJ, Lai C-S (1992) Synthetic Approaches to the Axane Family of Sesquiterpenoids. Total Synthesis of dl-Axamide-4, dl-Axisonitrile4, and dl-Axisothiocyanatc-4. J Org Chem 57: 2018
Guevel A-C, Hart DJ (1996) Synthesis of Carbocycles via Intramolecular Conjugate Additions: Total Syntheses of Axane Sesquiterpenoids. J Org Chem 61: 473
Ohkubo T, Akino H, Asaoka M, Takci H (1995) Total Synthesis of ()-Axamide-4 and ()-Axisonitrile-4. Tetrahedron Lett 36: 3365
Takeda K, Kubota T, Kawanami J (1960) Bile Acids and Steroids: XIII. Thio Steroids. 2. Addition of Thioeyanic to Steroidal a,ß-Unsaturated Ketones. J Chem Pharm Bull 8: 615 [Chen Abstr (1961) 55: 12450f]
Iwasawa N, Funahashi M, Narasaka K (1994) Total Synthesis of 10-Isothiocyanatoguaia-6-ene. Chem Lett 1697
Nakamura H, Ye B, Murai A (1992) Synthesis of (*)-Halipanicine, a Marine Sesquiterpene Isothiocyanate Isolated from an Okinawan Marine Sponge Halichondria panicea. Tetrahedron Lett 33: 8113
Ye B, Nakamura H, Murai A (1996) Total Synthesis of (+)-Halipanicine. Tetrahedron 52: 6361
Ichikawa Y (1991) First Synthesis of Theonellin Isocyanide. Synlett 3: 715
Hsieh SL, Chiu CT., Chang NC (1989) A Formal Total Synthesis of (±)-9-Isocyanopupukeanane. J Org Chem 54: 3820
Corey EJ, Ishiguro M (1979) Total Synthesis of (f)-2-Isocyanopupukeanane. Tetrahedron Lett 2745
Chang NC, Chang CK (1996) Total Synthesis of (f)-2-Pupukeanone. J Org Chem 61: 4967
Srikrishna A, Vijaykumar D, Sharma GVR (1997) A Short Vinyl Radical Cyclisation Approach to (f)-2-Pupukeanone. Tetrahedron Lett 38: 2003
Kaliappan K, Subba Rao GSR (1997) A New Total Synthesis of 2-Pupukeanone. Tetrahedron Lett 38: 2185
Benn M (1977) Glucosinolates. Pure Appl Chem 49: 197
Conn EE (1979) Biosynthesis of Cyanogenic Glycosides. Naturwissenschaften 66: 28
Conn EE (1981) Cyanogenic Glycosides. In: Conn EE (ed) The Biochemistry of Plants, a Comprehensive Treatise, vol 7. Academic Press, New York, pp 479–500
Eyjólfsson R (1970) Recent Advances in the Chemistry of Cyanogenic Glycosides. Fortschr Chem Org Naturstoffe 28: 74
Wratten SJ, Faulkner DJ (1977) Carbonimidic Dichlorides from the Marine Sponge Pseudaxinyssa pays. J Am Chem Soc 99: 7367
Wratten SJ, Faulkner DJ, Van Engen D, Clardy J (1978) A Vinyl Carbonimidic Dichloride from the Marine Sponge Pseudaxinyssa pitys. Tetrahedron Lett 1391
Wratten SJ, Faulkner DJ (1978) Minor Carbonimidic Dichlorides from the Marine Sponge Pseudaxinyssa pitys. Tetrahedron Lett 1395
Simpson JS, Raniga P, Garson MJ (1997) Biosynthesis of Dichloroimines in the Tropical Marine Sponge Stylotella aurantium. Tetrahedron Lett 38: 7947
Pala G, Mantegani A, Coppi G (1969) Terpene Compounds as Drugs. VI. Acyclic Mono-and Sesquiterpene Thiocyanates and Isothiocyanates. J Med Chem 12: 725
Li C, Blackman AJ (1994) Cylindricines CG, Perhydropyrrolo[2,1-j]quinolin-7-one Alkaloids from the Ascidian Clavelina cylindrica. Aus J Chem 47: 1355
Li C, Blackman AJ (1995) Cylindricines HK, Novel Alkaloids from the Ascidian Clavelina cylindrica. Aus J Chem 48: 955
Davidson B (1993) Ascidians: Producers of Amino Acid Derived Metabolites. Chem Rev 93: 1771
Karuso P, Scheuer PJ (1987) Long-chain a,w-Bisisothiocyanates from a Marine Sponge. Tetrahedron Lett 28: 4633
Jimenez C, Crews P (1991) Novel Marine Sponge Derived Amino Acids 13. Additional Psammaplin Derivatives from Psammaplysilla purpurea. Tetrahedron 47: 2097
Teeyapant R, Woerdenbag HJ, Kreis P, Hacker J, Wray V, Witte L, Proksch P (1993) Antibiotic and Cytotoxic Activity of Brominated Compounds from the Marine Sponge Verongia aerophoba. Z Naturforsch C: Biosci 48: 939
Ciminiello P, Fattorusso E, Magno S, Pansini M (1994) Chemistry of Verongida Sponges, III. Constituents of a Caribbean Verongula Sp. J Nat Prod 57: 1564
Albrizio S, Ciminiello P, Fattorusso E, Magno S, Pansini M (1994) Chemistry of Verongida Sponge Pseudoceratina crassa. Tetrahedron 50: 783
Ciminiello P, Fattorusso E, Magno S, Pansini M (1995) Chemistry of Verongida Sponges, IV. Comparison of the Secondary Metabolite Composition of Several Specimens of Pseudoceratina crassa. J Nat Prod 58: 689
Fattorusso E, Minale L, Sodano G (1972) Aeroplysinin-I, an Antibacterial Bromo-Compound from the Sponge Verongia aerophoba. J Chem Soc, Perkin 116
Fattorusso E, Minale L, Sodano G (1970) Aeroplysinin-I, a New Bromo-compound from Aplysina aerophoba. J Chem Soc, Chem Commun 751
Fulmor W, Van Lear GE, Morton GO, Mills RD (1970) Isolation and Absolute Configuration of the Aeroplysinin I. Enantiomorphic Pair from lanthella ardis. Tetrahedron Lett 4551
Colsulich DB, Lovell M (1971) An X-ray Determination of the Structure of an Antibacterial Compound from the Sponge, lanthella ardis. Chem Commun 397
Andersen RJ, Faulkner DJ (1975) Synthesis of Aeroplysinin-1 and Related Compounds. J Am Chem Soc 97: 936
Carney JR (1990) The Biosynthesis of Dibromotyrsine-derived Metabolites by Aplysinalistularis PhD Thesis. University of Illinois, Urbana, IL
Carney JR, Rinehardt KL (1995) Biosynthesis of Brominated Tyrosine Metabolites by Aplysina fistularis. J Nat Prod 58: 971
Gopichand Y, Schmitz FJ (1980) Bursatellin: A New Diol Dinitrile from the Sea Hare Bursatella leachii pleii. J Org Chem 45: 5383
Cimino G, Gavagnin M, Sodano G, Spinella A, Strazzullo G, Schmitz FJ, Gopichand Y (1987) Revised Structure of Bursatellin. J Org Chem 52: 2301
Racioppi R, Gavagnin M, Strazzullo G, Sodano G (1990) Stereochemistry and Synthesis of Bursatellin from Chloroamphenicol. Tetrahedron Lett 31: 573
Kawakami K, Takeuchi R, Miyashita M, Inci H, Shimamoto K, Ohfune Y (1991) Synthesis of ()-Bursatellin, a Metabolite from the Sea Hare (Bursatella sp). Chem Pharm Bull 39: 3170
Tsukamoto S. Kato H. Hirota H, Fusetani N (1996) Ceratinamine: An Unprecedented Antifouling Cyanoformamide from the Marine Sponge Pseudoceratina purpurea. J Org Chem 61: 2936
Schoenfeld RC, Ganem B (1998) Synthesis of Ceratinamine and Moloka’iamine: Antifouling agents from the Marine Sponge Pseudoceratina purpurea. Tetrahedron Lett 39: 4147
Hamann MT, Scheuer PJ (1991) Cyanopuupehenol, an Antiviral Metabolite of a Sponge of the Order Verongida. Tetrahedron Lett 32: 5671
Hamann MT, Scheuer PJ, Kelly-Borges M (1993) Biogenetically Diverse, Bioactive Constituents of a Sponge, Order Verongida: Bromotyramines and SesquiterpeneShikimatc Derived Metabolites. J Org Chem 58: 6565
Nasu SS, Yeung BKS, Hamann MT, Scheuer PJ, Kelly-Borges M, Goins K (1995) Puupehenone-Related Metabolites from Two Hawaiian Sponges, Hyrtios spp. J Org Chem 60: 7290
Rasmussen TJ, Jensen J, Anthoni U, Christophersen C, Nielsens PH (1993) Structure and Synthesis of Bromoindoles from the Marine Sponge Pseudosuberites hyalinus. J Nat Prod 56: 1553
Kato Y, Fusetani N, Matsunaga S, Hashimoto K (1985) Bioactive Marine Metabolites IX. Mycalisines A and B, Novel Nucleosides which Inhibit Cell Division of Fertilized Starfish Eggs, from the Marine Sponge Mycale sp. Tetrahedron Lett 26: 3483
Meade EA, Krawczyk SH, Townsend LB (1988) A Total Synthesis of the Naturally Occurring Pyrrolo[2,3-d]pyrimidine Nucleoside Mycalisine A. Tetrahedron Lett 29: 4073
Kato Y, Fusetani N, Matsunaga S, Hashimoto K, Fujita S, Furuya T (1986) Calyculin A, a Novel Antitumor Metabolite from the Marine Sponge Discodermia calyx. J Am Chem Soc 108: 2780
Kato Y, Fusetani N, Matsunaga S, Hashimoto K, Koseki K (1988) Isolation and Structure Elucidation of Calyculins B, C, and D, Novel Antitumor Metabolites, from the Marine Sponge Discodermia calyx. J Org Chem 53: 3930
Matsunaga S, Fujiki H, Sakata D, Fusetani N (1991) Calyculins E. F, G, and H, Additional Inhibitors of Protein Phosphatases I and 2A, from the Marine Sponge Discodermia calyx. Tetrahedron 47: 2999
Matsunaga S, Fusetani N (1991) Absolute Stereochemistry of the Calyculins, Potent Inhibitors of Protein Phosphatases 1 and 2A. Tetrahedron Lett 32: 5605
Suganuma M, Fujiki H, Furuya-Suguri H, Yoshizawa S, Yasumoto S, Kato Y, Fusetani N, Sugimura T (1990) Calyculin A, an Inhibitor of Protein Phosphatases, a Potent Tumor Promoter on CD-I Mouse Skin. Cancer Res 50: 3521
Okada A, Watanabe K, Umeda K, Miyakado M (1991) Calyculin E and F, Novel Insecticidal Metabolites, from the Marine Sponge, Discodermia sp. Agric Biol Chem 55: 2765
Matsunaga S, Wakimoto T, Fusetani N, Suganuma M (1997) Isolation of Dephosphono-calyculin A from the Marine Sponge, Discodermia calyx. Tetrahedron Lett 38: 3763
Munro M, Fusetani N, personal communication, 37th Annual Meeting, Amer Soc Pharmacognosy, Santa Cruz 37th Annual Meeting, Amer Soc Pharmacognosy, Santa Cruz, July 30, 1996
Dumdei EJ, Blunt JW, Munro MHG, Pannell LK (1997) Isolation of Calyculins, Calyculinamides, and Swinholide H from the New Zealand Deep-Water Marine Sponge Lamellomorpha strongylata. J Org Chem 62: 2636
Matsunaga S, Wakimoto T, Fusetani N (1997) Isolation of Four New Calyculins from the Marine Sponge, Discodermia calyx. J Org Chem 62: 2640; Ibid (1997) 62: 9388
Evans DA, Gage JR, Leighton JL (1993) Total Synthesis of the Enzyme Inhibitor (+)-Calyculin A. J Am Chem Soc 114: 9434
Evans DA, Gage JR (1992) Asymmetric Synthesis of Calyculin A. 1. The C1C25 Spiroketal Fragment. J Org Chem 57: 1958
Evans DA, Gage JR, Leighton JL, Kim AS (1992) Asymmetric Synthesis of Calyculin A. 2. The C26–C37 7-Amino Acid Fragments. J Org Chem 57: 1961
Evans DA, Gage JR, Leighton JL (1992) Asymmetric Synthesis of Calyculin A. 3. Assemblage of the Calyculin Skeleton and the Introduction of a New Phosphate Monoester Synthesis. J Org Chem 57: 1964
Hamada Y, Tanada Y, Yokokawa F, Shioiri T (1991) Stereoselective Syntheses of 2,3-Dihydroxy-4-dimethylamino-5-methoxypentanoic Acid, A Fragment of Calyculins Determination of the Absolute Configurations of Calyculins. Tetrahedron Lett 32: 5983
Yokokawa F, Hamada Y, Shioiri T (1992) Synthesis of the Oxazole Part of Calyculins; Part 1. Synlett 149
Yokokawa F, Hamada Y, Shioiri T (1992) Synthesis of the Oxazole Part of Calyculins; Part 2. Synlett 151
Yokokawa F, Hamada Y, Shioiri T (1992) Synthesis of the C26–C37 Fragment of Calyculin A Having Natural Configuration. Synlett 703
Yokokawa F, Hamada Y, Shioiri T (1996) Total Synthesis of Calyculin A Construction of the C(9)C(37) Fragment. J Chem Soc, Chem Commun 871
Smith AB, Salvatore BA, Hull KG, Duan JJ-W (1991) Calyculin Synthetic Studies. Stereocontrolled Assembly of the C(9)-C(13) Dithiane and C(26)C(37) Oxazole Intermediates. Tetrahedron Lett 32: 4859
Smith AB, Duan JJ-W, Hull KG, Salvatore BA (1991) Calyculin Synthetic Studies. Stereoselective Construction of the C(14)C(25) Spiroketal Subunit. Tetrahedron Lett 32: 4855
Salvatore BA, Smith III AB (1994) Calyculin Synthetic Studies. 3. Enantiomeric Purity Determination for the C(26)C(32) Oxazole Segment via the Silks-Odom 77Se NMR Method. Tetrahedron Lett 35: 1329
Smith III AB, Friestad GK, Duan JJ-W, Barbosa J, Hull KG, lwashima M, Qiu Y, Spoors PG, Bertounesquc E, Salvatore BA (1998) Total Synthesis of (+)-Calyculin A and ()-Calyculin B. J Org Chem 63: 7596
Koskinen AMP, Chen J (1991) Enantiospecific Synthesis of Polyhydroxy Amino Acids. Synthesis of the C33–C38 Portion of Calyculins. Tetrahedron Lett 32: 6977
Koskinen AMP, Pihko PM (1994) Calyculins. Asymmetric Synthesis of the C26–C32 Fragment. Tetrahedron Lett 35: 7417
Pihko PM, Koskinen AMP (1998) Studies of the C26–C32 Oxazole Fragment of Calyculin C: A Test Case for Oxazole Syntheses. J Org Chem 63: 92
Tanimoto N, Gerritz SW, Sawabe A, Noda T, Filla SA, Masamune S (1994) The Synthesis of Naturally Occurring ()-Calyculin A. Angew. Chem Int Ed Engl 33: 673
Zhao Z, Scarlato GR, Armstrong RW (1991) Synthesis of Trans-4-alkenyl Oxazoles. Tetrahedron Lett 32: 1609
Ogawa AK, DeMattei JA, Scarlato GR, Tellew JE, Chong LS, Armstrong RW (1996) Asymmetric Synthesis of Calyculin C. 2. Synthesis of the C26–C37 Fragment and Model Wittig Coupling. J Org Chem 61: 6153
Scarlato GR, DeMattei JA, Chong LS, Ogawa AK, Sin MR, Armstrong RW (1996) Asymmetric Synthesis of Calyculin C. 1. Synthesis of the C1C25 Fragment. J Org Chem 61: 6139
Barrett AGM, Malecha JW (1994) Synthetic Studies on Calyculin A A Convenient Asymmetric Synthesis of anti-Vicinal Diols. J Chem Soc, Perkin Trans 11901
Baldwin JE, Bansal HS, Chondrogianni J, Field LD, Taha AA, Thaller V. Brewer D, Taylor A (1985) Biosynthesis of 3-(3’-Isocyanocyclopent-2-enylidene)propionic Acid by Trichoderma hamatum (Bon.) Bain. aggr. Tetrahedron 41: 1931
Hagedorn I, Eholzer U, Lüttringhaus A (1960) Beiträge zur Konstitutionsermittlung des Antibiotikums Xanthocillin. Chem Ber 93: 1584
Achenbach H, Strittmatter H, Kohl W (1972) Die Strukturen der Xanthoxilline YI and Y2. Chem Ber 105: 3061
Achenbach H, Grisebach H (1965) Zur Biogenese des Xanthocillins. Z Naturforsch 20B: 137
Takatsuki A, Suzuki S, Ando K, Tamura G, Arima K (1968) New Antiviral Antibiotics; Xanthocillin X Mono-and Dimethylether, and Methoxyxanthocillin X Dimethylether. I. Isolation and Characterization. J Antibiot 21: 671
Ando K, Tamura G, Arima K (1968) A New Antibiotic, 1-(p-Hydroxyphenyl)-2,3diisocyano-4-(p-methoxyphenyl)-buta-1,3-diene. II. Elucidation of the Structure. J Antibiot 21: 587
Ando K, Suzuki S, Takatsuki A, Arima K, Tamura G (1968) A New Antibiotic, 1-(p-Hydroxyphenyl)-2,3-Diisocyano-4-(p-methoxyphenyl)-buta-1,3-diene. I. Isolation and Biological Properties. Studies on Antiviral and Antitumor Antibiotics. J Antibiot 21: 582
Kitahara N, Endo A (1981) Xanthocillin X Monomethyl Ether, a Potent Inhibitor of Prostaglandin Biosynthesis. J Antibiot 34: 1556
Büchi G, Luki KC, Kobbe B, Townsend JM (1977) Four New Mycotoxins of Aspergillus clavatus Related to Tryptoquivaline. J Org Chem 42: 244
Pfeifer S, Bär H, Zarnack J (1972) Über Stoffwechselprodukte der Xanthocillin (Brevicid) bildenden Mutante von Penicillium notatum Westl. Pharmazie 27: 536 [Chem Abstr (1972) 77: 161845j]
Tsunakawa M, Ohkusa N, Kobaru S, Narita Y, Murata S, Sawada Y, Old T (1993) BU-4704, a New Member of the Xanthocillin Class. J Antibiot 46: 687
Breinholt J, Kjær A, Olsen CE, Rassing BR (1996) A Bis-formamidodiphenylbutadiene from the Fungus Hamigera avellanea. Acta Chem Scand 50: 643
Ishida M, Hamasaki T, Hatsuda Y (1975) The Structure of Two New Metabolites, Emerin and Emericellin, from Aspergillus nidulans. Agric Biol Chem 39: 2181
Takahashi H, Nozawa K, Kawai K (1996) Isolation and Structures of Dicyanide Derivatives, Epurpurins A to C, from Emericella purpurea. Chem Pharm Bull 44: 2227
Morino T, Nishimoto M, Itou N, Nishikiori T (1994) NK372135s, Novel Antifungal Agents Produced by Neosartoria fischeri. J Antibiot 47: 1546
Zapf S, Hoßfeld M, Anke H, Velten R, Steglich W (1995) Darlucins A and B, New Isocyanide Antibiotics from Sphaerellopsis fzlum (Darluca filum). J Antibiot 48: 36
Jp. Kokai 110,658 (1989). See ref. (24), cited as footnote.
Takahashi C, Sekita S, Yoshihira K, Natori S (1976) The Structures of Toxic Metabolites of Aspergillus candidus. II. The Compound B (Xanthoascin), a Hepatoand Cardiotoxic Xanthocillin Analog. Chem Pharm Bull 24: 2317
Tamura A, Kotani H, Naruto S (1975) Trichoviridin and Dermadin From Trichoderma sp, TK-1. J Antibiot 28: 161
Brewer D, Gabe EJ, Hanson AW, Taylor A, Keeping JW, Thaller V, Das BC (1979) Isonitrile Acids from Cultures of the Fungus Trichoderma hamatum (Bon.) Bain. aggr., X-Ray Structure. J Chem Soc, Chem Commun 1061
Fujiwara A, Okuda T, Matsuda S, Shiomi Y, Miyamoto C, Sekini Y, Tazoe M, Fujiwara M (1982) Fermentation, Isolation and Characterization of Isonitrile Antibiotics. Agric Biol Chem 46: 1803
Baldwin JE, Adlington RM, Chondrogianni J, Edenborough MS, Keeping JW, Ziegler CB (1985) Structure and Synthesis of New Cyclopentenyl Isonitriles from Trichoderma hamatum (Bon.) Bain. aggr. HLX 1379. J Chem Soc, Chem Commun 816
Boyd RK, McAlees AJ, Taylor A, Walter JA (1991) Isolation of New Isocyanide Metabolites of Trichoderma hamatum as their (r15-Pentamethylcyclopentadienyl)or (r15-Ethyltetra-methylcyclopentadienyl)-di-µ-thiocyanato-rhodium Complexes. J Chem Soc, Perkin Trans 1 1461
Fukuyama T, Yung YM (1981) Total Synthesis of (f)-Methyl 3-(3-isocyano-6-oxabicyclo[3.1.0]hex-2-en-5-yl)-2-propenoate. Tetrahedron Lett 22: 3759
Ohsugi K, Ichida J, Takahashi E (1984) Antibiotic Compound. Ger Offen DE 3,326–518. [Chem Abstr (1984) 100: 137374c]
Yamano T, Hemmi S, Yamamoto I, Tsubaki K (1970) Patent Jpn. Kokai 45–15435
Nobuhara M, Tazima H, Shudo K, Itai A, Okamoto T, Iitaka Y (1976) A Fungal Metabolite, Novel Isocyano Epoxide. Chem Pharm Bull (Japan) 24: 832
Ollis WD, Rey M, Godtfredsen WO, Rastrup-Andersen N, Vangedal S, King TJ (1980) The Constitution of the Antibiotic Trichoviridin. Tetrahedron 36: 515
Baldwin JE, Adlington RM, O’Neil IA, Russell AT, Smith ML (1996) The Total Synthesis of (f)-Trichoviridin. J Chem Soc, Chem Commun 41
Baldwin JE, Aldous DJ, Chan C, Harwood LM, O’Neil IA, Peach JM (1989) The Total Synthesis of (f)-Isonitrin B (Deoxytrichoviridin). Synlett 9
Baldwin JE, Kelly DR, Ziegler CB (1984) The Synthesis of a Fungal Isonitrile Antibiotic via a Novel Radical Addition-Elimination Reaction. J Chem Soc, Chem Commun 133
Baldwin JE, O’Neil IA, Russell AT (1991) Isonitrin A: Revision of the Structure and Total Synthesis in Racemic Form. Synlett 551
Cited by Edenborough MS, Herbert RB (1987) (1).
Lee CH, Koshino H, Chung MC, Lee HJ, Kho YH (1995) MR304A, a New Melanin Synthesis Inhibitor Produced by Trichoderma harzianum. J Antibiot 48: 1168
Lee CH, Chung MC, Lee HJ, Bae KS, Kho YH (1997) MR566A and MR566B, New Melanin Synthesis Inhibitors Produced by Trichoderma harzianum. I. Taxonomy, Fermentation, Isolation and Biological Activities. J Antibiot 50: 469
Lee CH, Koshino H, Chung MC, Lee HJ, Hong JK, Yoo JS, Kho YH (1997) MR566A and MR566B, New Melanin Synthesis Inhibitors Produced by Trichoderma harzianum. II Physico-chemical Properties and Structural Elucidation. J Antibiot 50: 474
Parker WL, Rathnum ML, Johnson JH, Wells JS, Principe PA, Sykes RB (1988) Aerocyanidin, a New Antibiotic Produced by Chromobacterium violaceum. J Antibiot 41: 454
Sugawara T, Shibazaki M, Shimizu Y, Sasaki T, Imai Y (1993) New Antibiotics Y-03559J-A and Y-03559J-B from Micromonospora sp. Jpn. Kokai Tokkyo Koho JP 07 02,821 [95 02,821] (Cl. C07D303/48), 06 Jan 1995, Appl 93/171,081, 17 Jun 1993. [Chem Abstr (1995) 122: 263680s]
Sugawara T, Tanaka A, Imai H, Nagai K, Suzuki K (1997) Y-47515, a Novel Isonitrile Antibiotic from Micromonospora echinospora subsp. echinospora. J Antibiot 50: 944
Mori Y, Kohchi Y, Noguchi H, Suzuki M, Carmeli S, Moore RE, Patterson GML (1991) Isotatic Polymethoxy-l -Alkenes from the Terrestrial Blue-Green Algae Scytonema ocellatwn: Structure and Synthesis. Tetrahedron 47: 4889
Mori Y, Kohchi Y, Suzuki M, Carmeli S, Moore RE, Patterson GML (1991) Isotatic Polymethoxy 1-Alkenes from the Blue-Green Algae. Synthesis and Absolute Stereochemistry. J Org Chem 56: 631
Mori Y, Kawajiri N, Furukawa H, Moore RE (1994) Synthesis and Absolute Configuration of an Isotactic Nonamethoxy-l-pentacosene from the Blue-Green Algae Scytonema ocellatum. Tetrahedron 50: 11133
Gloer JB, Poch GK, Short DM, McCloskey DV (1988) Structure of Brassicicolin A: A Novel Isocyanide Antibiotic from the Phylloplane Fungus Alternaria brassicicola. J Org Chem 53: 3758
Ciegler A, Lindenfelser LA (1969) An Antibiotic Complex from Alternaria brassicicola. Experientia 25: 719
Boeck LD, Hoehn MM, Sands TH, Wetzel RW (1978) A32390A, A New Biologically Active Metabolite. I. Discovery and Fermentation Studies. J Antibiot 31: 19
Marconi GG, Molloy BB, Nagarajan R, Martin JW, Deeter JB, Occolowitz JL (1978) A32390A, A New Biologically Active Metabolite. II. Isolation and Structure. J Antibiot 31: 27
Turner JR, Butler TF, Gordee RS, Thakkar AL (1978) A32390A, A New Biologically Active Metabolite. III. In Vitro and In Vivo Antifungal Activity. J Antibiot 31: 33
Marquez JA, Horan AC, Kalyanpur M, Lee BK, Loebenberg D, Miller GH, Patel M, Waitz JA (1983) The Hazimicins, A New Class of Antibiotics. Taxonomy, Fermentation, Isolation, Characterization and Biological Properties. J Antibiot 36: 1101
Wright JJK, Cooper AB, McPhail AT, Merrill Y, Nagabhushan TL, Puar MS (1982) X-ray Crystal Structure Determination and Synthesis of the New Isonitrilecontaining Antibiotics, Hazimycin Factors 5 and 6. J Chem Soc, Chem Commun 1188
Evans JR, Napier EJ, Yates P (1976) Isolation of a New Antibiotic from a Species of Pseudomonas J Antibiot 29: 850
Kobayashi J, Tsuda M, Nemoto A, Tanaka Y, Yazawa K, Mikami Y (1997) Brasilidine A, a New Cytotoxic Isonitrile-containing Indole Alkaloid from the Actinomycete Nocardia brasiliensis. J Nat Prod 60: 719
Isshiki K, Takahashi Y, Okada M, Sawa T, Hamada M, Naganawa H, Takita T, Takeuchi T, Umezawa H, Yamamoto M, Tatsuta K (1987) A New Antibiotic Indisocin and N-Methylindisocin. J Antibiot 40: 1195
Isshiki K, Takahashi Y, Sawa T, Naganawa H, Takeuchi T, Umezawa H, Tatsuta K (1987) One-pot Preparation of 1-Chlorovinylisocyanides from Carbonyl Compounds. J Antibiot 40: 1199
Isshiki K, Takahashi Y, Sawa T, Naganawa H, Takeuchi T, Umezawa H, Tatsuta K (1987) Total Synthesis of Indisocin and N-methylindisocin. J Antibiot 40: 1202
Gmelin R, Virtanen I (1959) New Type of Enzymatic Cleavage of Mustard Oil Glucosides. Formation of Allyl Thiocyanate in Thlaspi arvense and Benzyl Thiocyanate in Lepidium ruderale and L. sativum. Chem Scand 13: 1474
Schlüter M, Gmelin R (1972) Abnormale Enzymatische Spaltung von 4-Methylthiobutyl-glucosinolat in Frischpflanzen von Eruca sativa. Phytochemistry 11: 3427
Cheung KK, Kjær A, Sim GA (1965) The Absolute Configuration of Sulphoxide Mustard Oils. J Chem Soc, Chem Commun 100
Mislow K, Green MM, Laur P, Chisholm DR (1965) Optical Rotatory Dispersion and Absolute Configuration of Dialkyl Sulfoxides. J Am Chem Soc 87: 665
Schmid H, Karrer P (1948) Syntheses der Racemischen und der Optisch Aktiven Formen des Sulforaphans. HeIv Chim 31: 1497
Balenović K, Deljac A, Monković I, Štefanac Z (1966) Synthesis of (±) Sulphoraphene. Tetrahedron 22: 2139
Kawabata J, Fukushi Y, Hayashi R, Suzuki K, Mishima Y, Yamane A, Mizutani J (1989) 8-Methylsulfinyloctyl Isothiocyanate as an Allelochemical Candidate from Rorippa sylvestris Besser. Agric Biol Chem 53: 3361
Yamane AJ, Furikura J, Ogawa H, Mizutani J (1992) Isothiocyanates as Alleopathic Compounds from Rorippa indica Hiern. (Cruciferae) Roots. J Chem Ecol 18: 1941
Kjær A, Christensen B (1958) IsoThiocyanates XXX. Glucohirsutin, a New Naturally Occurring Glucoside Furnishing ()-8-Methylsulfinyloctyl isoThiocyanate on Enzymic Hydrolysis. Chem Scand 12: 833
Kjær A, Christensen B (1957) IsoThiocyanates XXVI. Straight-chain w-Methylthioalkyl Isothiocyanates and Some Derivatives. Chem Scand 11: 1298
Kjær A, Gmelin R (1956) IsoThiocyanates XXIII. L-()-10–9-Methylsulphinyldecyl Isothiocyanates, a New Mustard Oil Present as a Glucoside (glucocamelinin) in Camelina species. Chem Scand 10: 1358
Kjær A, Larsen I, Gmelin R (1955) IsoThiocyanates XIV. 5-Methylthiopentyl isoThiocyante, a New Mustard Oil Present in Nature as a Glucoside (Glucoberteroin). Chem Scand 9: 1311
Tang C-S, Takenaka T (1983) Quantitation of a Bioactive Metabolite in Undisturbed Rhizosphere-Benzyl Isothiocyanate from Carica Papaya L. J Chem Ecol 9: 1247
Tang C-S, Tang WJ (1976) Inhibition of Papain by Isothiocyanates. Biochim Biophys Acta 452: 510
Kosemura S, Yamamura S, Hasegawa K (1993) Chemical Studies of 4-Methylthio3-butenyl Isothiocyanate from Roots of Japanese Radish (Raphanus sativus L) in Connection with Raphanusanins, Phototropism-Regulating Substances of Radish Hypocotyls. Tetrahedron Lett 34: 481
Cole RA (1976) Isothiocyanates, Nitriles, and Thiocyanates as Products of Autolysis of Glucosinolates in Cruciferae. Phytochemistry 15: 759
Faizi S, Siddiqui BS, Saleem R, Siddiqui S, Aftab K, Gilani A-uI-H (1992) Isolation and Structure Elucidation of Novel Hypotensive Agents, Niazinin A, Niazinin B, Niazimicin and Niaziminin A + B from Moringa oleifera: The First Naturally Occurring Thiocarbamates. J Chem Soc, Perkin Trans 13237
Faizi S, Siddiqui BS, Saleem R, Siddiqui S, Aftab K, Gilani A-uI-H (1994) Isolation and Structure Elucidation of New Nitrile and Mustard Oil Glycosides from Moringa oleifera and their Effect on Blood Pressure. J Nat Prod 57: 1256
Faizi S, Siddiqui BS, Saleem R. Siddiqui S, Aftab K, Gilani A-uI-H (1994) Novel Hypotensive Agents, Niazimin A, Niazimin B, Niazicin A and Niazicin B from Moringa oleifera: Isolation of First Naturally Occurring Carbamates. J Chem Soc, Perkin Trans 13035
Kjær A, Malver O, el-Menshawi B, Reisch J (1979) Isothiocyanates in MyrosinaseTreated Seed Extracts of Moringa peregrina. Phytochemistry 18: 1485
Nahrstedt A, Jensen PS, Wray V (1989) Prunasin-6’-malonate, a Cyanogenic Glucoside from Merremia disserta. Phytochemistry 28: 623
Nahrstedt A, Jensen PS, Wray V, Wald B, Galensa R, Herrmann K (1989) Malonylprunasin, a Cyanogenic Glycoside from Merremia dissecta and Other Malonated Flavonol Glycosides from Pyrus communis. Phytochemistry 28: 663
Nahrstedt A, Rockenbach J (1993) Occurrence of the Cyanogenic Glucoside Prunasin and its Corresponding Mandelic Acid Amide Glucoside in Olinia Species (Oliniaceae). Phytochemistry 34: 433
Lechtenberg M, Nahrstedt A, Fronczek FR (1996) Leucine-derived Nitrile Glucosides in the Rosaceae and their Systematic Significance. Phytochemistry 41: 779
Powell RG, Mikolajczak KL. Zilkowski BW, Lu HSM, Mantus EK, Clardy J (1991) Dithyreanitrile: an Unusual Insect Antifeedant from Dithyrea wislizenii. Experientia 47: 304
Mantus EK, Clardy J (1993) The Synthesis of Dithyreanitrile. Tetrahedron Lett 34: 1085
Naruse N, Yamamoto S, Yamamoto H, Kondo S, Masuyoshi S, Numata K-I, Fukagawa Y, Oki T (1993) (3-Cyanoglutamic acid, a New Antifungal Amino Acid from a Streptomycete. J Antibiot 46: 685
Fushiya S, Sato S, Kusano G, Nozoe S (1993) (3-Cyano-L-alanine and N-(y-Lglutamy1)43-cyano-L-alanine, Neurotoxic Constituents of Clitocybe acromelalga. Phytochemistry 33: 53
Delaere IM, Tate ME, Jones GP., Tiekink ERT (1995) N-y-L-Glutamyl-(3-cyano-Lalanine, an Antinutritional Factor ex Vicia catira L, as its Ammonium Salt. Acta Crystallogr Sect C: Cryst Struct Commun 51: 289
Olafsdottir ES., Andersen JV, Jaroszewski JW (1989) Cyanohydrin Glycosides of Passifloraceae. Phytochemistry 28: 127
Olafsdottir ES, Cornett C, Jaroszewski JW (1989) Structures of Passicapsin and Passibiflorin, Cyclopentenoid Cyanohydrin Glycosides from Passiflora capsularis. Chem Scan, Ser B 43: 51
Jaroszewski JW, Andersen JV, Billeskov I (1987) Plants as a Source of Chiral Cyclopentenes: Taraktophyllin and Epivolkenin, New Cyclopentenoid Cyanohydrin Glucosides from Flacourtiaceae. Tetrahedron 43: 2349
Jaroszewski JW, Bruun D, Clausen V, Cornett C (1988) Novel Cyclopentenoid Cyanohydrin Rhamnoglucosides from Flacourtiaceae. Planta Med 54: 333
Clapp RC, Ettlinger MG, Long Jr L (1970) Deidaclin: A Natural Glucoside of Cyclopentenone Cyanohydrin. J Am Chem Soc 92: 6378
Spencer KC, Seigler DS (1984) The Cyanogenic Glycoside Barterin from Barteria fistulosa is Epitetraphyllin B. Phytochemistry 23: 2365
Jaroszewski JW, Jensen B (1985) Deidaclin and Tetraphyllin A, Epimeric Glucosides of 2-Cyclopentenone Cyanohydrin, in Adenia globosa spp. globosa Engl. (Passifloraceae). Crystal Structure of Deidaclin Tetraacetate. Chem Scan, Ser B 39: 867
Gainsford GJ, Russell GB, Reay PF (1984) Absolute Configuration of Tetraphyllin B, a Cyanoglucoside from Tetrapathaea tetrandra. Phytochemistry 23: 2527
Fukuyama T (1992) Synthesis of Naphthyridinomycin. In: Advances in Heterocyclic Natural Product Synthesis 2: 189
Zmijewski Jr. MJ, Mikolajczak M, Viswanatha V, Hruby VJ (1982) Biosynthesis of the Antitumor Naphthyridinomycin. J Am Chem Soc 104: 4969
Kluepfel D, Baker HA, Piattoni G, Sehgel SN, Sidorowicz A, Singh K, Vezina C (1975) Naphthyridinomycin, a New Broad-Spectrum Antibiotic. J Antibiot 28: 497
Sygusch J, Brisse F, Hanessian S (1976) The Crystal and Molecular Structure of Naphthyridinomycin, C21H27N3O6, a Broad Spectrum Antibiotic. Cryst B32: 1139
Hayashi T, Noto T, Nawata Y, Sawada M, Ando K (1982) Cyanocyclin A, A New Antibiotic. Taxonomy of the Producing Organism, Fermentation, Isolation, and Characterization. J Antibiot 35: 771
Hayashi T, Nawata Y (1983) X-ray Crystallographic Determination of the Molecular Structures of the Antibiotic Cyanocyclin A and Related Compounds. J Chem Soc Perkin Trans II, 335
Gould SJ, He W, Cone MC (1993) New Cyanocyclines from a Cyanide-treated Broth of Streptomyces lusitanus. J Nat Prod 56: 1239
Stewart JB, Bornemann V, Chen JL, Moore RE, Caplan FR, Karuso H, Larson LK, Patterson GML (1988) Cytotoxic, Fungicidal Nucleosides from Blue Green Algae Belonging to the Scytonemataceae. J Antibiot 41: 1048
Nishimura H, Katagiri K, Sato K, Mayama M, Shimaoka N (1956) Toyocamycin, a New Anti-candida Antibiotic. J Antibiot, ser A 9: 60
Tolman RL, Robins RK, Townsend LB (1969) Pyrrolopyrimidine Nucleosides. III. The Total Syntheses of Toyocamycin, Sangivamycin, Tubercidin and Related Derivatives. J Am Chem Soc 91: 2102
Tolman RL, Robins RK, Townsend LB (1968) Pyrrolo[2,3-djpyrimidine Nucleoside Antibiotics. Total Synthesis and Structure of Toyocamycin, Unamycin B, Vengicide, Antibiotic E-212, and Sangivamycin (BA-90912) J Am Chem Soc 90: 524
Hagedorn I, Eholzer U, Etling H (1965) Isonitrile, V. Darstellung von a,(3-Ungesättigten Isonitrilen, 3-Keto-und 3-Chloro-isonitrilen. Syntheses des Xanthocillin Dimethyläthers. Chem Ber 98: 193
Hagedorn I, Eholzer U (1965) Isonitrile, VI. Dehydro-Dimerisierung von wAcylamino-acetophenonen. Beitrag zur Total Synthese des Xanthocillin-Dimethyläthers. Chem Ber 98: 202
Hagedorn I, Eholzer U (1962) Synthesis of Xanthocillin Dimethyl Ether. Angew Chem, Int Ed 1: 212
Baldwin JE, Derome AE, Field LD, Gallagher PT, Taha AA, Thaller V, Brewer D, Taylor A (1981) Biosynthesis of a Cyclopentyl Dienyl Isonitrile Acid in Cultures of the Fungus Trichoderma hamatum (Bon.) Bain. aggr. J Chem Soc, Chem Commun, 1227
Wüst HH, Bardenhagen J. Schöllkopf U (1985) Synthese des Antibiotikums A32390A [1,6-Di-O-(-2-isocyan-3-methylcrotonoyl)-D-mannit] und einiger Strukturvarianten. Liebigs Ann Chem 1825
Hoppe I, Schöllkopf U (1984) Synthesis and Biological Activities of the Antibiotic B371 and its Analogs. Liebigs Ann Chem 600
Garson MJ (1989) Biosynthetic Studies on Marine Natural Products. Nat Prod Rep 6: 143
Garson MJ (1993) The Biosynthesis of Marine Natural Products. Chem Rev 93: 1699
Chang CWJ, Scheuer PJ (1990) Biosynthesis of Marine Isocyanoterpenoids in Sponges. Comp Biochem Physiol 97B: 227
Bornemann V. Patterson GML, Moore RE (1988) Isonitrilc Biosynthesis in the Cyanophyte Hapalosiphon fontinalis. J Am Chem Soc 110: 2339
Carson MJ, Larsen R. Thompson JE, Bergquist PR (1988) Terpenes as Structural Components in Sponge Cell MembranesExperimental Evidence from Cell Separation and Membrane Fractionation Studies with the Tropical Marine Spotnge Amphimeron sp. Aus Mar Sci Assoc Jubilee Conference 19631988), 149
Garson MJ, Partali V, Liaaen-Jensen S, Stoilov IL (1988) Isoprenoid Biosynthesis in a Marine Sponge of the Amphimedon Genus: Incorporation Studies with [1–14C]-acetate, [4–14C]cholesterol and [2–14C]mevalonate. Comp Biochem Physiol 91B: 293
Simpson JS, Garson MJ (1999) Advanced Precursors in Marine Biosynthetic Study: The Biosynthesis of Diisocyanoadociane in Amphimedon terpenesi,s. Tetrahedron Lett 40: 3909
Karuso P, Scheuer PJ (1989) Biosynthesis of Isocyanoterpenes in Sponges. J Org Chem 54: 2092
Hagadone MR. Scheuer PJ, Holm A (1984) On the Origin of the Isocyano Function in Marine Sponges. J Am Chem Soc 106: 2447
Tengo A, Santacroce C, Sodano G (1979) Metabolism in Porifera. X. On the Intermediary of a Formamide Moiety in the Biosynthesis of Isonitrile Terpenoids in Sponges. Experientia 35: 10
Cable KM, Herbert RB, Knaggs AR, Mann J (1991) The Biosynthesis of Xanthocillin-X Monomethyl Ether in Dichotomomyces cejpii. Experiments on the Origin of the Isocyanide Carbon Atoms. J Chem Soc, Perkin Trans 1 595
Herbert RB, Mann JM (1983) Biosynthesis of Tuberin from Tyrosine and Glycine. J Chem Soc, Chem Commun 1008
Herbert RB, Mann J (1984) Biosynthesis of Tuberin and Xanthocillin from Tyrosine. Tetrahedron Lett 25: 4263
Herbert RB, Mann J (1984) The Incorporation of C1 Units in the Biosynthesis of Tuberin and Xanthocillin. J Chem Soc, Chem Commun 1474
Cable KM, Herbert RB, Mann JM (1987) On the Biosynthesis of the Fungal Isocyanide, Xanthocillin Monomethyl Ether. Tetrahedron Lett 28: 3159
Cable KM, Herbert RB, Bertram V, Young DW (1987) Stereochemistry Associated With the Conversion of C-3 of Serine Through Methylenetetrahydrofolate and Methenyltetrahydrofolate in the Biosynthesis of Tuberin. Tetrahedron Lett 28: 4101
Cable KM, Herbert RB, Mann J (1987) The Biosynthesis of Tuberin from Tyrosine and Glycine; Observations on the Stereochemistry Associated with the Conversion of Glycine through Methylenetetrahydrofolate into Methenyltetrahydrofolate. J Chem Soc, Perkin Trans 11593
Parry RJ, Buu HP (1982) XXXXXX Biosynthesis of an Isonitrile Acid from Trichoderma Hamatum Tetrahedron Lett 23: 1435
Puar MS, Munayyer H, Hedge V, Lee BK, Waitz JA (1985) The Biosynthesis of Hazimicins: Possible Origin of Isonitrile Carbon. J Antibiot 38: 530
Davis RH, Nahrstedt A (1987) A Biosynthesis of Cyanogenic Glucosides in Butterflies and Moths. Effective Incorporation of 2-Methylpropanenitrile and 2-Methylbutanenitrile Into Linamarin and Lotaustralin by Zygaena and Heliconius Species (Lepidoptera). Insect Biochem 17: 689
Monde K, Takasugi M, Ohnishi T (1994) Biosynthesis of Cruciferous Phytoalexins. J Am Chem Soc 116: 6650
Valeriote F, Moore RE, Patterson GML, Paul VP, Scheuer PJ, Corbett T (1994) Discovery of Anticancer Agents from Natural Products. In: Valeriote FA, Corbett TH, Baker LH (eds) Discovery and Development of Anticancer Agents. Kluwer Academic Publishers, Norwell, MA, pp 1–25
Fu X, Schmitz FJ (1999) 7-Hydroxyceratinamine, a New Cyanoformide-Containing Metabolite from a Sponge, Aplysinella sp. J Nat Prod 62: 1072
Matsunaga S, Wakimoto T, Fusetani N (1997) Structure and Biological Activity of New Calyculins Isolated from the Marine Sponge Discodermia calyx. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 181 [Chem Abstr (1999) 131: 85653m]
Simpson JS, Garson MJ (1998) Thiocyanate biosynthesis in the Tropical Marine Sponge Axinyssa n.sp. Tetrahedron Lett 39: 5819
Tanaka J, Higa T (1999) Two New Cytotoxic Carbonimidic Dichlorides from the Nudibranch Reticulidia fungia. J Nat Prod 62: 1339
Ho T-L, Kung L-R (1999) Stereoselective Synthesis of 2-Isocyanoallopupukeanane Org Lett 1: 1051
Ho T-L, Gour HJ (1999) Total Synthesis of 9-Isocyanoneopupukeanane. J Org Chem 64: 8965
Fusetani N (1997) Marine Natural Products Influencing Larval Settlement and Metamorphosi of Benthic Invertebrates. Current Org Chem 1: 127
König GM, Wright AD (1999) GC-MS and NMR Analysis of the Nudibranch Phyllidiella pustulosa and One of its Dietary Components the Sponge Phakellia carduus. Intern Cong Natural Prod Res, Amsterdam, July 26–31, Abstr. 354
Goclik E, König GM, Wright AD (1999) Collection and Secondary Metabolite Investigations of Marine Organisms from the Two Azorean Islands Faial and St. Jorge. Intern Cong Natural Prod Res, Amsterdam, July 26–31, Abstr. 352
Sung K (1999) Isomerization Energies of Isocyanides and Nitriles. J Org Chem 64: 8984
Gregory RJH (1999) Cyanohydrins in Nature and the Laboratory: Biology, Preparations and Synthetic Applications. Chem Rev 99: 3649
Wood JL, Weiss MM, Ovaska TV, Korakas P (2000) Progress Towards the Total Synthesis of Welwitindolinone A isonitrile: Construction of the Carbon Skeleton, 219th ACS Meeting, San Francisco, Abstr 847
Wood JL, Holubec AA, Stolz BM, Weiss MM, Dixon JA, Doan BD, Shamji MF, Chen JM, Heffron TP (1999) Application of Reactive Enols in Synthesis: A Versatile, Efficient, and Stereoselective Construction of the Welwitindolinone Carbon Skeleton. J Am Chem Soc 121: 6326
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Chang, C.W.J. (2000). Naturally Occurring Isocyano/Isothiocyanato and Related Compounds. In: Herz, W., Falk, H., Kirby, G.W., Moore, R.E. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 80. Springer, Vienna. https://doi.org/10.1007/978-3-7091-6331-3_1
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