Abstract
The term “polyketide” was coined in 1907 by Collie (37) and later defined more explicitly by Birch (13) to describe the aromatic natural products which are formed in nature from acetic acid via β-polycarbonyl intermediates. Biosynthetically, the polyketides arise by the acyl polymalonate route, which also produces the fatty acids. The latter are formed from linear arrays of acetate units but not via polycarbonyl intermediates.
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References
Acker, T. E., P. E. Brenneisen, and S. W. Tanenbaum: Isolation, Structure, and Radiochemical Synthesis of 3,6-Dimethyl-4-hydroxy-2-pyrone. J. Amer. Chem. Soc. 88, 834 (1966).
Allport, D. C., and J. D. Bu’lock: Biosynthetic Pathways in Daldinia concentrica. J. Chem. Soc. (London) 1960, 654.
Arndt, F., B. Eistert, H. Scholz und E. Aron: Zur Synthese der Dehydracetsäure aus Acetessigester. Ber. Dtsch. chem. Ges. 69, 2373 (1936).
Baeyer, A.: Über die Synthese des Acetessigäthers und des Phloroglucins. Ber. Dtsch. chem. Ges. 18, 3454 (1885).
Baker, P. M., and B. W. Bycroft: A Convenient Route to Some Naturally Occurring Hydroxynaphthaquinones. Chem. Commun. 1968, 71.
Balenović, K., and R. Munk: Polyoxo Compounds. III. sym-Dibenzoylacetone (1,3,5-Trioxo-1,5-diphenylpentane). Arhiv Kern. 18, 41 (1946); [Chem. Abstr. 42, 2926 (1948)].
Balenović, K., und D. Sunko: Über γ-Benzoyl-acetessigsäure. Monatsh. Chem. 79, 1 (1948).
Bedford, C. T., J. L. Douglas, B. E. Mccarry, and T. Money: Pyrone Studies: Conversion of 2-Pyrones into Aromatic Compounds. Chem. Commun. 1968, 1091.
Bedford, C. T., and T. Money: Photochemistry of 4-Hydroxy-6-methyl-(2H)-pyran-2-one (Triacetic Acid Lactone). Chem. Commun. 1969, 685.
Bentley, R., and P. M. Zwitkowits: Biosynthesis of Tropolones in Penicillium stipitatum. VII. The Formation of Polyketide Lactones and Other Nontropolone Compounds as a Result of Ethionine Inhibition. J. Amer. Chem. Soc. 89, 676 (1967).
Bethell, J. R., and P. Maitland: Organic Reactions in Aqueous Solution at Room Temperature. Part III. The Influence of pH on the Self-condensation of Diacetylacetone: Constitution of Collie’s Naphthalene Derivative. J. Chem. Soc. (London) 1962, 3751.
Birch, A. J.: Biosynthetic Relations of Some Natural Phenolic and Enolic Compounds. Fortschr. Chem. organ. Naturstoffe 14, 186 (1957).
_ Some Pathways in Biosynthesis. Proc. Chem. Soc. (London) 1962, 3.
Birch, A. J., D. W. Cameron, and R. W. Rickards: Studies in Relation to Biosynthesis. Part XXIII. The Formation of Aromatic Compounds from β-Polyketones. J. Chem. Soc. (London) 1960, 4395.
Birch, A. J., and F. W. Donovan: Studies in Relation to Biosynthesis. I. Some Possible Routes to Derivatives of Orcinol and Phloroglucinol. Austral. J. Chem. 6, 360 (1953).
Birch, A. J., P. Fitton, D. C. C. Smith, D. E. Steere, and A. R. Stelfox: Studies in Relation to Biosynthesis. Part XXXII. Preparation, Spectra, and Hydrolysis of Poly-β-carbonyl Compounds. J. Chem. Soc. (London) 1963, 2209.
Birch, A. J., R. A. Massy-Westropp, and C. J. Moye: Studies in Relation to Biosynthesis. VII. 2-Hydroxy-6-methylbenzoic Acid in Penicillium griseofulvum Dierckx. Austral. J. Chem. 8, 539 (1955).
Birch, A. J., R. A. Massy-Westropp, R. W. Rickards, and H. Smith: Studies in Relation to Biosynthesis. Part XIII. Griseofulvin. J. Chem. Soc. (London) 1958, 360.
Birch, A. J., O. C. Musgrave, R. W. Rickards, and H. Smith: Studies in Relation to Biosynthesis. Part XX. The Structure and Biosynthesis of Curvularin. J. Chem. Soc. (London) 1959, 3146.
Birch, A. J., J. F. Snell, and P. J. Thomson: Studies in Relation to Biosynthesis. Part XXVIII. Oxytetracycline (Terramycin). J. Chem. Soc. (London) 1962, 425.
Boltze, K.-H., und K. Heidenbluth: Zur Synthese 3-substituierter 4-Hydroxypyrone-(2), I. Ringschlüsse mit Malonsäure-dichloriden. Chem. Ber. 91, 2849 (1958).
Borsche, W., und C. K. Bodenstein: Untersuchungen über die Bestandteile der Kawawurzel, IX.: Die Synthese des Yangonins. Ber. Dtsch. chem. Ges. 62, 2515 (1929).
Bram, G.: Synthese d’un derive du trioxo-3,5,7 octanoate d’ethyle modele chimique de biosynthese de l’orcinol. Tetrahedron Letters 1967, 4069.
Brown, K. S., D. W. Cameron, and U. Weiss: Chemical Constituents of the Bright Orange Aphid, Aphis Nerii Fonscolombe. I. Neriaphin and 6-Hydroxymusizin 8-O-β-Z)-Glucoside. Tetrahedron Letters 1969, 471.
Bruice, T. C., and B. Holmquist: The Establishment of a Carbanion Mechanism for Ester Hydrolysis and the Unimportance of Electrostatic Effects of α Substituents on the Rates of Hydroxide Ion Attack at the Ester Carbonyl Group. J. Amer. Chem. Soc. 90, 7136 (1968).
Bu’lock, J. D., and H. G. Smith: Pyrones. Part I. Methyl Ethers of Tautomeric Hydroxypyrones and the Structure of Yangonin. J. Chem. Soc. (London) 1960, 502.
Bycroft, B. W., T. A. Dobson, and J. C. Roberts: Studies in Mycological Chemistry. Part VIII. The Structure of Flavasperone (“Asperxanthone”), a Metabolite of Aspergillus niger. J. Chem. Soc. (London) 1962, 40.
Bycroft, B. W., A. Hassaniali-Walji, A. W. Johnson, and T. J. King: The Structure and Synthesis of Barakol; a Novel Dioxaphenalene Derivative from Cassia siamea. J. Chem. Soc. C (London) 1970, 1686.
Carnduff, J., J. A. Miller, B. R. Stockdale, J. Larkin, D. C. Nonhebel, and H. C. S. Wood: Synthesis and Reactions of 3,3-Dimethylallyl Derivatives of Acetylacetone and Other Poly-β-carbonyl Compounds. J. Chem. Soc. (London) Perkin I, 1972, 692.
Casnati, G., A. Quilico, A. Ricca, and P. Vita-Finzi: New Synthesis of polyketones: 1,5-dibenzoylacetylacetone. Chim. et ind. 47, 993 (1965); [Chem. Abstr. 64, 8068 (1966)].
____ Some Synthetic Applications of the Reaction of Reductive Opening of the Isoxazole Ring. Tetrahedron Letters 1966, 233.
____ Synthesis of 5,3′-and 5,5′-Methylenediisoxazoles, Intermediates in the Preparation of β-Tetraketones. Gazz. chim. ital. 96, 1064 (1966); [Chem. Abstr. 66, 37811 (1967)].
Chauvelier, J.: Sur une nouvelle synthèse des pyrones. C. R. hebd. séances Acad. Sci. 226, 927 (1948).
Cheng, F. C., and S. F. Tan: Synthesis and Reactions of 7-Methylpyrano[4,3-b]-pyran-2,5-dione. J. Chem. Soc. (London) C 1968, 543.
Collie, J. N.: On the Constitution of Dehydracetic Acid. J. Chem. Soc. (London) 59, 179 (1891).
____ The Lactone of Triacetic Acid. J. Chem. Soc. (London) 59, 607 (1891).
____ Derivatives of the Multiple Ketene Group. Proc. Chem. Soc. (London) 23, 230 (1907).
____ Derivatives of the Multiple Keten Group. J. Chem. Soc. (London) 91, 1806 (1907).
Collie, J. N., and W. S. Myers: The Formation of Orcinol and other Condensation Products from Dehydracetic acid. J. Chem. Soc. (London) 63, 122 (1893).
Collie, J. N., and B. D. Steele: Dimethyldiacetylacetone, Tetramethylpyrone, and Orcinol Derivatives from Diacetylacetone. J. Chem. Soc. (London) 77, 961 (1900).
Comer, F. W., T. Money, and A. I. Scott: Conversion of a Polypyrone into Phenolic Compounds. Chem. Commun. 1967, 231.
Cornelius, H., und H. Von Pechmann: Über die Synthese des Orcins aus Aceton-dicarbonsäureäther. Ber. Dtsch. chem. Ges. 19, 1446 (1886).
Crombie, L., M. Eskins, and D. E. Games: Ratio-dependent Products from Xanthophanic Enol and Magnesium Methoxide; Reaction Control by Substrate-chelation. Chem. Commun. 1968, 1015.
Crombie, L., D. E. Games, and M. H. Knight: Structures of Xanthophanic and Glaucophanic Acid. Tetrahedron Letters 1964, 2313.
_____ Base-catalysed Cyclisation of Highly Enolisable Systems: Diversion of Pathway by Magnesium Chelation. Chem. Commun. 1966, 355.
_____ Polyketo-enols and Chelates. Part I. The Formation and Constitution of Xanthophanic Enol and the Xanthyrones. J. Chem. Soc. (London) C 1967, 757.
Crombie, L., D. E. Games, and M. H. Knight: Polyketo-enols and Chelates. Part II. The Chemistry of the Xanthophanic Enols. J. Chem. Soc. (London) C 1967, 763.
_____ Polyketo-enols and Chelates. Part III. The Constitution and Chemistry of the Glaucophanic Enols. J. Chem. Soc. (London) C 1967, 773.
_____ Polyketo-enols and Chelates. Part IV. The By-Product in the Xanthophanic-Glaucophanic Enol Reaction: 2-Acetyl-4,7-alkoxycarbonyl-1,6-dimethylnaphthalene. J. Chem. Soc. (London) C 1967, 777.
Crombie, L., and A. W. G. James: The Control of Pyrone and Aromatic Cyclisation in Polyketonic-Polyenolic Systems by Magnesium Alkoxide Concentration. Chem. Commun. 1966, 357.
Dean, F. M.: Naturally Occurring Oxygen Ring Compounds. London: Butterworth & Co. 1963.
Deshapande, S. S., Y. V. Dingankar, and D. N. Kopil: Synthesis and Structure of Dipropionylacetone and of Di-n-butyrylacetone. J. Indian Chem. Soc. 11, 595 (1934).
Douglas, J. L., and T. Money: Biogenetic-type Synthesis of Benzophenones and Biphenyls. Canad. J. Chem. 45, 1990 (1967).
_____ Pyrone Studies. II. Biogenetic-type Synthesis of Phenolic Compounds. Tetrahedron 23, 3545 (1967).
_____ Pyrone Studies. Linear α-Pyrone Route to Protected β-Polyketones. Canad. J. Chem. 46, 695 (1968).
Edwards, R. L., and D. V. Wilson: Constituents of the Higher Fungi. Part II. The Synthesis of Hispidin. J. Chem. Soc. (London) 1961, 5003.
Feist, F.: Über Dehydracetsäure. Liebigs Ann. Chem. 257, 253 (1890).
Frei, H., und H. Schmid: Inhaltstoffe aus Eleutherine bulbosa (Mill.) Urb. VIII. Synthese des Eleutherinols. Liebigs Ann. Chem. 603, 169 (1957).
Gatenbeck, S.: On the Biosynthesis of the Pigments of Penicillium islandicum. II. Acta Chem. Scand. 14, 296 (1960).
Gatenbeck, S., and P. Barbesgård: On the Biosynthesis of the Pigments of Penicillium islandicum. III. Acta Chem. Scand. 14, 230 (1960).
Gatenbeck, S., P. O. Eriksson, and Y. Hansson: Cell-free C-Methylation in Relation to Aromatic Biosynthesis. Acta Chem. Scand. 23, 699 (1969).
Gatenbeck, S., and S. Hermodsson: Enzymic Synthesis of the Aromatic Product Alternariol. Acta Chem. Scand. 19, 65 (1965).
Gatenbeck, S., and K. Mosbach: Acetate Carboxyl Oxygen (18O) as Donor for Phenolic Hydroxy Groups of Orsellinic Acid Produced by Fungi. Acta Chem. Scand. 13, 1561 (1959).
Gaucher, G. M., and M. G. Shepherd: Isolation of Orsellinic Acid Synthase. Biochem. Biophys. Res. Comm. 32, 664 (1968).
Geuther, A.: Untersuchungen über einbasische Kohlenstoffsäuren: 1. Über die Essigsäure. Z. Chem. (Jena) 2, 8 (1866); [Chem. Zbl. 37, 801 (1866)].
Goetschel, C., et C. Mentzer: Synthèse de nouveaux dérivés α-pyroniques par condensation thermique de quelques esters maloniques avec des cétones. Bull. soc. chim. France 1962, 365.
Gottlieb, O. R., and W. B. Mors: The Chemistry of Rosewood. III. Isolation of 5,6-Dehydrokavain and 4-Methoxyparacotoin from Aniba firmula Mez. J. Organ. Chem. (USA) 24, 17 (1959).
Guilford, H., A. I. Scott, D. Skingle, and M. Yalpani: The Synthesis of Tetraacetic Acid Lactone and a Model for the Biosynthesis of 6-Methylsalicylic Acid. Chem. Commun. 1968, 1127.
Hale, W. J.: The Constitution of Dehydroacetic Acid. J. Amer. Chem. Soc. 33, 1119 (1911).
Hampton, K. G., T. M. Harris, C. M. Harris, and C. R. Hauser: Condensations at the Terminal Methyl Group of 1,3,5-Triketones by Means of Sodamide in Liquid Ammonia. J. Organ. Chem. (USA) 30, 4263 (1965).
Harris, C. M., and T. M. Harris: Synthesis of 5-Oxohexenoic Acid. J. Organ. Chem. (USA) 36, 2181 (1971).
_____ Unpublished results.
Harris, T. M.: Unpublished results.
Harris, T. M., and R. L. Carney: Biogenetically Modeled Synthesis of β-Resorcylic Acids. J. Amer. Chem. Soc. 88, 2053 (1966).
_____ Biogenetic-Type Synthesis of an Acylphloroglucinol. J. Amer. Chem. Soc. 88, 5686 (1966).
_____ Synthesis of 3,5,7-Triketo Acids and Esters and Their Cyclizations to Resorcinol and Phloroglucinol Derivatives. Models of Biosynthesis of Phenolic Compounds. J. Amer. Chem. Soc. 89, 6734 (1967).
Harris, T. M., and C. S. Combs, Jr.: Synthesis of Certain Naturally Occurring 2-Pyrones via 3,5-Diketo Acids. J. Organ. Chem. (USA) 33, 2399 (1968).
Harris, T. M., and C. M. Harris: Carboxylation of β-Dicarbonyl Compounds through Dicarbanions. Cyclizations to 4-Hydroxy-2-pyrones. J. Organ. Chem. (USA) 31, 1032 (1966).
_____ Condensations at the 6-Methyl Position of Dehydracetic Acid. A Novel Site of Reactivity. Chem. Commun. 1966, 699.
_____ Condensations of 2,6-Diphenyl-4-pyrone with Carbanions. J. Organ. Chem. (USA) 32, 970 (1967).
_____ Lactonization of 3,5,7-Trioxo-7-phenylheptanoic Acid and its 2-Methyl Homolog. Tetrahedron 25, 2687 (1969).
Harris, T. M., C. M. Harris, and R. J. Light: The Isolation of Triacetic Acid Lactone from Cultures of Penicillium patulum. Biochim. Biophys. Acta 121, 420 (1966).
Harris, T. M., C. M. Harris, and M. P. Wachter: Condensations of Dehydroacetic Acid at the 6-Methyl Position. Tetrahedron 24, 6897 (1968).
Harris, T. M., T. T. Howarth, and R. L. Carney: Models of the Biogenesis of Polyketide-Type Phenolic Ethers. J. Amer. Chem. Soc. 93, 2511 (1971).
Harris, T. M., and G. P. Murphy: Synthesis of 1,3,5,7,9-Pentacarbonyl Compounds. J. Amer. Chem. Soc. 93, 6708 (1971).
Harris, T. M., and M. P. Wachter: Aromatization Reactions of 4-Hydroxy-6-phenacyl-2-pyrone and Related Compounds. Tetrahedron 26, 5255 (1970).
Harris, T. M., M. P. Wachter, and G. A. Wiseman: The Cleavage and Aromatic Recyclization of 4-Hydroxy-6-phenacyl-2-pyrone. A Novel Metallic Cation Effect. Chem. Commun. 1969, 177.
Hauser, C. R., and T. M. Harris: Condensations at the Methyl Group Rather than the Methylene Group of Benzoyl-and Acetylacetone Through Intermediate Dipotassio Salts. J. Amer. Chem. Soc. 80, 6360 (1958).
Hay, J. V.: Biogenetic-type Synthesis of Heptaketide Phenolic Natural Products: Alternariol and Lichexanthone. Dissert., Vanderbilt Univ. 1972.
Hay, J. V., and T. M. Harris: Biogenetic-type Syntheses of Heptaketide Natural Products: Alternariol and Lichexanthone. Chem. Commun. 1972, 953.
Hedgecock, P. F., P. F. G. Praill, and A. L. Whitear: Acid-catalysed Conversion of Pyronopyrones into Phenolic Ketones. Chem. and Ind. 1966, 1268.
Hillis, W. E., and N. Ishikura: An Enzyme from Eucalyptus which Converts Cinnamoyl Triacetic Acid into Pinosylvin. Phytochem. 8, 1079 (1969).
Hillis, W. E., and Y. Yazaki: The Biosynthesis of Stilbenes in Eucalypt Leaves. Phytochem. 10, 1051 (1971).
Howarth, T. T., and T. M. Harris: Methyl 2-Hydroxy-4-methoxy-6-phenylbenzoate and Methyl 2-Hydroxy-6-methoxy-4-phenylbenzoate; Reassignment of a Structure. Canad. J. Chem. 46, 3739 (1968).
Howarth, T. T., and T. M. Harris: Biogenetic-type Synthesis of β-Resorcylic Acids. Isolation and Characterization of the Aldol Intermediate. J. Amer. Chem. Soc. 93, 2506 (1971).
Howarth, T. T., G. P. Murphy, and T. M. Harris: Preparation and Biogenetic-Type Aromatizations of Tetraacetic Acid (3,5,7-Trioxooctanoic Acid). J. Amer. Chem. Soc. 91, 517 (1969).
Huckin, S. N., and L. Weiler: Claisen Condensation of the Dianion of β-Keto Esters. Tetrahedron Letters 1972, 2405.
Hünig, S., E. Benzing und K. Hübner: Synthesen mit Enaminen, VI. Reaktionen mit Diketen zu γ-Pyronen. Chem. Ber. 94, 486 (1961).
Iguchi, S., and K. Hisatsune: Pyrone Derivatives. I. Syntheses and Antibacterial Properties of Ethyl 4-Hydroxy-l-oxo-6-methyl-2-pyrone-3-decanoate and Related Compounds. J. Pharmac. Soc. Japan 77, 94 (1957); [Chem. Abstr. 51, 8733 (1957)].
Jerdan, D. S.: The Condensation of Ethylic Acetonedicarboxylate and Constitution of Triethylic Orcinoltricarboxylate. J. Chem. Soc. (London) 75, 808 (1899).
Jobst, J., und O. Hesse: Über die Cotorinden und ihre charakteristischen Bestandteile. Liebigs Ann. Chem. 199, 17 (1879).
Julia, M., et J. Bullot: Synthèses de la paracotoine et de quelques α-pyrones apparentées. Bull. soc. chim. France 1959, 1689.
____ Sur quelques alcools dichlorovinyliques et leur transformation en acide éthyléniques. Bull. soc. chim. France 1959, 1828.
Julia, M., et C. B. Du Jassonneix: Synthèse de la méthoxy-4 paracotoine et de quelques composés apparentés. C. R. hebd. séances Acad. Sci. 253, 872 (1961).
Kato, T., and T. Hozumi: Studies on Ketene and Its Derivatives. XLIX. Reaction of Diketene with β-Ketoesters to Give Ethyl Orsellinate, Divarate, Olivetol Carboxylate, and Sphaeropherol Carboxylate. Chem. Pharm. Bull. (Japan) 20, 1574 (1972).
Kirby, F. B., T. M. Harris, and C. R. Hauser: Acylation vs. Conjugate Addition of Dipotassio β-Diketones with Cinnamic Esters. Synthesis of Unsaturated 1,3,5-Triketones and t-Butyl 5,7-Dioxoalkanoates. J. Organ. Chem. (USA) 28, 2266 (1963).
Kögl, F., und C. A. Salemink: Untersuchungen über Derivate von 2,3-Dihydropyran-2,4-dion. (1. Mitteilung.) Rec. trav. chim. Pays-Bas 71, 779 (1952).
____ Untersuchungen über Derivate von 2,3-Dihydro-pyran-2,4-dion. (2. Mitteilung.) Rec. trav. chim. Pays-Bas 74, 221 (1955).
Komninos, T.: Nouveau mode de passage de la série grasse a la série aromatique. Bull. soc. chim. France [iv] 23, 449 (1918).
Lefeuvre, A., et C. Mentzer: Applications du phényl-thiomalonate d’éthyle en synthèse hétérocyclique. Bull. soc. chim. France 1964, 623.
Light, R. J.: The Biosynthesis of 6-Methylsalicylic Acid. J. Biol. Chem. 242, 1880 (1967).
Light, R. J., T. M. Harris, and C. M. Harris: Metabolism of Triacetic Acid and Triacetic Acid Lactone. Biochemistry 5, 4037 (1966).
Light, R. J., and C. R. Hauser: Aroylations of β-Diketones at the Terminal Methyl Group to Form 1,3,5-Triketones. Cyclizations to 4-Pyrones and 4-Pyridones. J. Organ. Chem. (USA) 25, 538 (1960).
Lynen, F., E. Reichert und L. Rueff: Zum biologischen Abbau der Essigsäure. VI. („Aktivierte Essigsäure“, ihre Isolierung aus Hefe und ihre chemische Natur.) Liebigs Ann. Chem. 574, 1 (1951).
Lynen, F., und M. Tada: Die biochemischen Grundlagen der „Polyacetat-Regel“. Angew. Chem. 73, 513 (1961).
Macierewicz, Z.: Synthesis of the Lactone of the Mother Substance of Yangonin. Roczniki Chem. 24, 144 (1950); [Chem. Abstr. 48, 10013 (1954)].
Marcus, E., J. F. Stephen, and J. K. Chan: A Study of the Acylation of 4-Hydroxy-6-methyl-2-pyrone and 4-Hydroxy-6-phenyl-2-pyrone. J. Heterocycl. Chem. 6, 13 (1969).
Mccormick, J. R. D.: Biosynthesis of the Tetracyclines. In: Z. Vaněk and Z. Hoštálek, Biogenesis of Antibiotic Substances, p. 73. Prague: Publishing House of the Czechoslovak Academy of Sciences 1965.
Mccormick, J. R. D., and E. R. Jensen: Biosynthesis of Tetracyclines. X. Protettone. J. Amer. Chem. Soc. 90, 7126 (1968).
Mccormick, J. R. D., E. R. Jensen, N. H. Arnold, H. S. Corey, U. H. Joachim, S. Johnson, P. A. Miller, and N. O. Sjolander: Biosynthesis of Tetracyclines. XI. The Methylanthrone Analog of Protetrone. J. Amer. Chem. Soc. 90, 7127 (1968).
Miles, M. L., T. M. Harris, and C. R. Hauser: Aroylation at the Terminal Methyl Group of a 1,3,5-Triketone to Form a 1,3,5,7-Tetraketone. J. Amer. Chem. Soc. 85, 3884 (1963).
____ Aroylations at the Methyl Group of Benzoylacetone and Related β-Diketones with Esters to Form 1,3,5-Triketones by Sodium Hydride. Other Terminal Condensations. J. Organ. Chem. (USA) 30, 1007 (1965).
Money, T.: Biogenetic-type Synthesis of Phenolic Compounds. Chem. Rev. 70, 553 (1970).
Money, T., F. W. Comer, G. R. B. Webster, I. G. Wright, and A. I. Scott: Pyrone Studies. I. Biogenetic-type Synthesis of Phenolic Compounds. Tetrahedron 23, 3435 (1967).
Money, T., J. L. Douglas, and A. I. Scott: Biogenetic-type Synthesis of Phenolic Compounds. J. Amer. Chem. Soc. 88, 624 (1966).
Money, T., I. H. Qureshi, G. B. Webster, and A. I. Scott: Chemistry of Polypyrones. A Model for Acetogenin Biosynthesis. J. Amer. Chem. Soc. 87, 3004 (1965).
Mors, W. B., O. R. Gottlieb, and C. Djerassi: The Chemistry of Rosewood. Isolation and Structure of Anibine and 4-Methoxyparacotoin. J. Amer. Chem. Soc. 79, 4507 (1957).
Mors, W. B., M. T. Magalhães, and O. R. Gottlieb: Naturally Occurring Aromatic Derivatives of Monocyclic α-Pyrones. Fortschr. Chem. organ. Naturstoffe 20, 131 (1962).
Mühlemann, H.: Anthraquinones and Anthraquinone Glycosides. XII. Nuclear Synthesis of the Emodins of Frangula and of a Chrysophanic Acid Isomer (1,6-Dihydroxy-3-methylanthraquinone). Pharm. Acta Helv. 26, 195 (1951). [Chem. Abstr. 46, 8078 (1952)].
Murphy, G. P.: Synthesis of Tetra-and Pentacarbonyl Compounds Using Lithium Diisopropylamide. Dissert., Vanderbilt Univ. 1971.
Murray, T. P., and T. M. Harris: Negatively Charged Electrophiles. Acylation of Strong Nucleophiles by Enolate Salts of β-Keto Esters. J. Amer. Chem. Soc. 94, 8253 (1972).
____ Unpublished results.
Ollis, W. D., I. O. Sutherland, R. C. Codner, J. J. Gordon, and G. A. Miller: The Incorporation of Propionate in the Biosynthesis of ε-Pyrromycinone (Rutilan-tinone). Proc. Chem. Soc. (London) 1960, 347.
O’sullivan, W. I., and C. R. Hauser: Certain Condensations at the Terminal Methyl Group of 3-Phenylpentane-2,4-dione through Its Dipotassio Derivative. Cyclizations. J. Organ. Chem. (USA) 25, 1110 (1960).
Pike, D. G., J. J. Ryan, and A. I. Scott: Synthesis and Aromatisation of the Linear Hepta-β-carbonyl System. Chem. Commun. 1968, 629.
Pollak, J.: Notiz über das Cotoin. Monatsh. Chem. 22, 996 (1901).
Praill, P. F. G., and A. L. Whitear: The Acid-catalysed Self-condensation of Acetic Anhydride and Analogous Compounds. Proc. Chem. Soc. (London) 1961, 112.
Rassweiler, C. F., and R. Adams: The Structure of Dehydroacetic Acid. J. Amer. Chem. Soc. 46, 2758 (1924).
Resplandy, A.: Synthèse et propriétés de deux α-pyrones permettant d’accéder à la méthoxy-4, paracotoine. Étude de quelques substances apparentées. Bull. soc. chim. France 1962, 1332.
Rittenberg, D., and K. Bloch: The Utilization of Acetic Acid for Fatty Acid Synthesis. J. Biol. Chem. 154, 311 (1944).
Robinson, Sir Robert: The Structural Relations of Some Plant Products. J. Roy. Soc. Arts 96, 795 (1948).
Ruhemann, S.: The Formation of 4-Pyrone Compounds from Acetylenic Acids. Part I. J. Chem. Soc. (London) 93, 431 (1908).
____ The Formation of 4-Pyrone Compounds from Acetylenic Acids. Part II. J. Chem. Soc. (London) 93, 1281 (1908).
Schmidt, U., und M. Schwochau: β-Polycarbonylverbindungen, 3. Mitt.: Über Synthesen mit den Trimethylsilylestern der Acetessigsäure und Malonsäure. Ein neuer Weg zu Diacyl-methanen und Diacyl-essigsäureestern. Monatsh. Chem. 98, 1492 (1967).
Scott, A. I., H. Guilford, J. J. Ryan, and D. Skingle: Biogenetic-type Synthesis of Polyketides. Part VIII. Experiments with the Tetra-and Hexa-acetate Systems. Tetrahedron 27, 3025 (1971).
Scott, A. I., H. Guilford, and D. Skingle: Biogenetic-type Synthesis of Polyketides. Part IX. A Model for the Biosynthesis of 6-Methyl Salicylic Acid. Tetrahedron 27, 3039 (1971).
Scott, A. I., D. G. Pike, J. J. Ryan, and H. Guilford: Biogenetic-type Synthesis of Polyketides. Part X. Synthesis and Reactions of Hepta-and Nona-β-Carbonyl Chains as Substrate Models. Tetrahedron 27, 3051 (1971).
Semmler, F. W., und E. Schossberger: Zur Kenntnis der Bestandteile ätherischer Öle. (Zusammensetzung des ätherischen Öles von Xanthoxylum aubertia Cordemoy [Evodia aubertia Cordemoy] und Xanthoxylum alatum Roxb.) Ber. Dtsch. chem. Ges. 44, 2885 (1912).
Sjöland, S., and S. Gatenbeck: Studies on the Enzyme Synthesizing the Aromatic Product Alternariol. Acta Chem. Scand. 20, 1053 (1966).
Smith Laboratories, T. and H.: Further Note on Brevifolin. Pharm. J. 123, 604 and 611 (1929); [Chem. Abstr. 24, 2547 (1930)].
Soliman, G., and I. E. El-Kholy: The Pyrone Series. Part I. 2:6-Diaryl-4-pyrones. J. Chem. Soc. (London) 1954, 1755.
Sproxton, F.: The Esters of Triacetic Lactone and Triacetic Acid. J. Chem. Soc. (London) 89, 1186 (1906).
Stadtman, E. R., M. Doudoroff, and F. Lipmann: The Mechanism of Acetoacetate Synthesis. J. Biol. Chem. 191, 377 (1951).
Steglich, W., and W. Reininger: A Synthesis of Endocrocin, Endocrocin-9-anthrone and Related Compounds. Chem. Commun. 1970, 178.
Stephen, J. F., and E. Marcus: A Facile Route to a Novel Derivative of 2,4,6,8-Nonanetetraone. J. Organ. Chem. (USA) 35, 258 (1970).
Stetter, H., und S. Vestner: Synthese des 2,4,6-Trioxa-adamantan-Ringsystems. Chem. Ber. 97, 169 (1964).
Stewart, A. W.: Recent Advances in Organic Chemistry, vol. II, 5th edition, chapt. IX. London: Longmans, Green & Co. 1927.
Stout, G. H., D. L. Dreyer, and L. H. Jensen: Structure of Rubrofusarin. Chem. and Ind. 1961, 289.
Thomas, R.: The Biosynthesis of Alternariol. Proc. Chem. Soc. (London) 1959, 88.
Tobias, P. S., and F. J. Kézdy: The Alkaline Hydrolysis of 5-Nitrocoumaranone. A Method for Determining the Intermediacy of Carbanions in the Hydrolysis of Esters with Labile α Protons. J. Amer. Chem. Soc. 91, 5171 (1969).
Towers, G. H. N.: Metabolism of Phenolics in Higher Plants and Micro-organisms. In: J. B. Harborne, Biochemistry of Phenolic Compounds, p. 249. New York: Academic Press, Inc. 1964.
Van Tamelen, E. E.: Biogenetic-type Syntheses of Natural Products. Fortschr. Chem. Organ. Naturstoffe 19, 242 (1961).
Vorländer, O., and G. A. Meyer: Überführung des Dibenzal-acetons in α,α-Diphenylpyron. Ber.Dtsch. chem. Ges. 45, 3355 (1912).
Wachter, M. P., and T. M. Harris: Condensations at the 6α-Position of Triacetic Lactone Via the Dianion. Tetrahedron 26, 1685 (1970).
Wakil, S. J., and J. Ganguly: On the Mechanism of Fatty Acid Synthesis. J. Amer. Chem. Soc. 81, 2597 (1959).
Wiley, R. H., C. H. Jarboe, and H. G. Ellert: 2-Pyrones. XV. Substituted 3-Cinnamoyl-4-hydroxy-6-methyl-2-pyrones from Dehydroacetic Acid. J. Amer. Chem. Soc. 77, 5102 (1955).
Winzheimer, E.: Investigation of Kava Root. Arch. Pharmaz. 246, 338 (1908); [Chem. Abstr. 3, 429 (1909)].
Wittek, P. J., and T. M. Harris: Unpublished results.
Wittek, P. J., K. B. Hindley, and T. M. Harris: Synthesis of C-Methyl Derivatives of 1-Phenyl-1,3,5-hexanetrione. J. Organ. Chem. (USA) 38, 896 (1973).
Witter, R. F., and E. Stotz: Synthesis and Properties of Triacetic Acid. J. Biol. Chem. 176, 485 (1948).
Wolfe, J. F., T. M. Harris, and C. R. Hauser: Condensations at the Methyl Group of Ethyl Acetoacetate by Means of Potassium Amide or Sodium Hydride. J. Organ. Chem. (USA) 29, 3249 (1964).
Woods, L. L., and P. A. Dix: Acylation, Bromination and Oxidation of 4-Pyrones and Pyronones. J. Organ. Chem. (USA) 26, 2588 (1961).
Woods, L. L., D. Johnson, and F. Thomas: 6-Aryl-5-carboxy-4-hydroxy-2-pyrones. Texas J. Science 19, 227 (1967); [Chem. Abstr. 68, 21777 (1968)].
Work, S. D., and C. R. Hauser: Acylations of Dilithio β-Diketones with Aliphatic Esters to Form 1,3,5-Triketones. Cyclizations to 4-Pyrones and 4-Pyridones. J. Organ. Chem. (USA) 28, 725 (1963).
Yamamura, S., K. Kato, and Y. Hirata: The Reaction of 6-Carboxymethyl-4-methoxy-2-pyrone with Acetic Anhydride. Chem. Commun. 1968, 1580.
____ Reactions of 4-Methoxy-2-oxopyran-6-ylacetic Acid With Acid Anhydrides. J. Chem. Soc. (London) C 1969, 2461.
Ziegler, E., und H. Junek: Synthesen von Heterocyclen. XI. Mitteilung: 4-Hydroxy-2-pyrone. Monatsh. Chem. 89, 323 (1958).
Ziegler, E., und E. Nölken: Synthesen von Heterocyclen. XII. Mitteilung: Über das Anibin. Monatsh. Chem. 89, 391 (1958).
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Harris, T.M., Harris, C.M., Hindley, K.B. (1974). Biogenetic-Type Syntheses of Polyketide Metabolites. In: Herz, W., Grisebach, H., Kirby, G.W. (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 31. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7094-6_5
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