Abstract
The glutarimide antibiotics constitute a group of near-neutral naturally-occurring substances whose discovery was heralded in 1946 by the isolation of a substance, called actidione (later changed to cy cloheximide: vide infra) from a streptomycin-producing strain of Streptomvices griselts (129). Although this material displayed little or no activity against the usual pathogenic bacteria, it was found to be very effective in inhibiting the growth of many fungi. The characteristic feature of these antibiotics is the 3-ethylglutarimide group which is substituted at only the β-position of the ethyl group.
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References
Acitelli, M. A.: Actidione. The Synthesis of the Glutarimide Moiety. Ph. D. Thesis, Cornell University, 1957.
Anet, F. A. L.: Nuclear Magnetic Resonance Spectra of Compounds Containing C-Methyl Groups. Canad. J. Chem. 39, 2262 (1961).
Barondes, S. H.: Cerebral Protein Synthesis Inhibitors Block Long-Term Memory. Int. Rev. Neurobiol. 12, 177 (197o).
Barondes, S. H.: In Protein Metabolism of the Nervous System. Ed., A. Lajtha Plenum Press, New York, 545 (197o)
Beard, C., C. Djerassi, J. Sicher, P. Sipos, and M. Ticiey: Optical Rotatory Dispersion Studies. Lxxxi. Stereochemical Studies. Xxvii. Conformational Distortion in 2-Methylcyclohexanones. Tetrahedron 19, 919 (1963).
Bennett, L. L., V. L. Ward and R. W. Brockman: Inhibition of Protein Synthesis in vitro by Cycloheximide and Related Glutarimide Antibiotics. Biochim. Biophvs. Acta 103, 478 (1965).
Bhacca, N. S., and D. H. Williams: Solvent Effects in Nmr Spectroscopy Iii. Chemical Shifts Induced by Benzene in Ketones. Tetrahedron 21, 2021 (1965).
Cation, D.: Actidione Stops Cherry Leaf Spot Fungus. Amer. Fruit Grower 74 29 (1954).
Churchill, B. W. Production of Cycloheximide. United States Patent 2885326 (1959).
Cohen, H. D., and S. H. Barondes: Puromycin and Cycloheximide. Different Effects on Hippocampal Electrical Activity. Science 154. 1557 (1966).
Cohen, H. D., and S. H. Barondes: Puromycin Effect on Memory may be due to Occult Seizures. Science 157, 333 (1967).
Connolly, J. D., and R. Mc Crindle: Nuclear Magnetic Resonance Solvent Shifts of Methyl Groups in Alicyclic Ketones: Pyrrole and Other Aromatic Solvents. J. Chem. Soc. ( London ) 1966, 1613.
Corey, E. J., and R. A. Sneen: Stereoelectronic Control in EnolizationKetonization Reactions. J. Amer. Chem. Soc. 78, 6269 (1956).
Cudlív, J., M. Pi 7A, M. Vondr.IèEK, Z. VanÉK and R. W. RIcxArds: Metabolites of Streptomyces noursei. Viii. Biogenesis of Cycloheximide from the Point of View of the Glutarimide Ring Symmetry. Folia Microbiol. IS, 376 (1967).
Eble, T. E., M. E. Bergy, R. R. Herr and J. A. Fox: The Separation and Properties of the Streptovitacins. Antibiotics and Chemotherapy 10, 479 (196o).
Eble, T. R., M. E. Bergy, C. M. Large, R. R. Herr and W. G. Jackson: Isolation Purification and Properties of Streptovitacins-A and -B. Antibiotics Annual 1958–1959 New York, Medical Encyclopedia Inc. 1959. 555.
Egawa, Y., S. Oshima and S. Umezawa: Studies on Cycloheximide-Related Compounds. I. Esters of Cycloheximide and Their Antitoxoplasmic Activity. J. Antibiotics (Japan) Ser. A 18, 171 (1965).
Egawa, Y., M. Suzuki and T. Okuda: Studies on Streptonlvices Antibiotic, Cycloheximide. Xvi. Synthesis of Cycloheximide Analogous Compounds. Chem. Pharm. Bull. (Tokyo) 11, 589 (1963).
Egawa, Y., and S. Umezawa: Studies of Cycloheximide-Related Compounds II. The Acid-Catalyzed Condensation of Glutarimide-fl-Acetaldehyde with Ketones. Bull. Chem. Soc. Japan 38, 2169 (1965).
Eisenbraun, E. J., J. OsIecki and C. Djerassi: On the Absolute Configuration of the Antibiotic Actidione. J. Amer. Chem. Soc. 8o, 1261 (1958).
Ennis, H. L.: Structure Activity Studies with Cycloheximide and Congeners. Biochem. Pharm. 17, 1197 (1968).
Evans, J. S., G. D. Mengel, J. Ceru and R. L. Johnston: Biological Studies on Streptovitacin-A New Antitumor Agent. Antibiotics Annual 1958–1959 New York, Medical Encyclopedia Inc. 1959 565.
Field, J. B., A. Mireles, H. R. Pachl, L. Bascoy, L. Cano and W. K. Bul Loci(: Experimental Evaluation of a New Antitumor Agent, Streptovitacin-A. Antibiotics Annual 1958–19$9, New York, Medical Encyclopedia Inc. 1959, 572.
Ford, J. H., and W. Klomparens: Cycloheximide (Actidione) and its Nonagricultural Uses. Antibiotics and Chemotherapy 10, 682 (t96o).
Ford, J. H., W. Klomparens and C. L. Hamner: Cycloheximide (Actidione) and its Agricultural Uses. Plant Disease Reptr. 42, 68o (1958).
Ford, J. H., and B. E. Leach: Actidione an Antibiotic from Streptornyces griseus. J. Amer. Chem. Soc. 7o, 1223 (1948).
FoRist, A. A., and S. Theal: Spectrophotometric Determination of Cycloheximide. Analyt. Chem. 31, 1042 (1959).
Frohardt, R. P., H. W. Dion, Z. L. Jakubowski, A. Ryder, J. C. French and Q. R. Bartz: Chemistry of Streptimidone, A New Antibiotic. J. Amer. Chem. Soc. 81, 5500 (1959).
Garrett, E. R., and R. E. Notars: Cycloheximide Transformations. II. Kinetics and Stability in a Pharmaceutically Useful pH Range. J. Pharm. Sci. 54, 209 (1965).
Garrett, E. R., and R. E. Notars: Determination of Cycloheximide and its Degradation Products Alone and in Mixtures. J. Pharm. Sci. 54, 561 (1965).
Garrett, E. R., and R. E. Notars: Cycloheximide Transformations. I. Kinetics and Mechanism in Aqueous Acid. J. Organ. Chem. (U. S. A.) 31, 425 (1966).
Geller, A., F. Robustelli, S. H. Barondes, H. D. Cohen and M. E. Jarvik: Impaired Performance by Post-Trial Injections of Cycloheximide in a Possive Avoidance Task. Psychopharmacologia (Berl.) 14, 371 (5969).
Geller, A., F. Robustelli and M. E. Jarvik: A Parallel Study of the Amnesic Effects of Cycloheximide and Ecs Under Different Strengths of Conditioning. Psychopharmacologia (Berl.) 16, 281 (197o).
Grollman, A. P.: Structural Basis for Inhibition of Protein Synthesis by Emetine and Cycloheximide Based on an Analogy Between Ipecac Alkaloids and Glutarimide Antibiotics. Proc. Nat. Acad. Sci. U. S. A. 56, 1867 (1966).
Hamilton, J. M., M. Szkolnik and E. Sondheimer: Systemic Control of Cherry Leaf Spot Fungus by Foliar Sprays of Actidione Derivatives. Science 123, 1175 (1956).
Hennis, H. E., L. G. Duquette and F. Johnson: Glutarimide Antibiotics. Xiii. Comment on the Stereochemistry of Streptovitacin-A and E-73. J. Organ. Chem. (U.S.A.) 33, 904 (1968).
Herr, R. R.: Structures of the Streptovitacins. J. Amer. Chem. Soc. 81, 2595 (1959).
Herr, R. R. Structure Studies on Streptovitacins-A and -B. Antibiotics Annual 1958–1959, New York, 3ledical Encyclopedia Inc. 1959, 56o.
Highet, R. J. and V. Prelog: Stoffwechselprodukte von Actinomycetin. Actiphenol. Hely. Chim. Acta 42, 1523 (1959).
Igarashi, S., and S. Wada Fermicidin, A New Antibiotic Active AgainstYeasts and Trichomonas. J. Antibiotics (Japan), Ser. B 7, 221 (1954)
Johnson, F.: Glutarimide Antibiotics. I. The Sy nthesis of Actiphenol. J Organ. Chem. (U. S. A.) 27, 3658 (1962).
Johnson, F., and A. A. Carlson: Glutarimide Antibiotics. Part Viii. A Stereo-elective Synthesis of dl-A-Epiisocycloheximide. Tetrahedron Letters 1965, 885.
Johnson, F., A. A. Carlson and N. A. StarxovsxY: Glutarimide Antibiotics. NI. A Total Synthesis of dl-A-Epiisocycloheximide. J. Organ. Chem. (U. S. A.) 31, 1327 (1966).
Johnson, F., W. D. GuROwItz and N. A. Starkovsky: Glutarimide Antibiotics. Part II. The Synthesis and Stereochemistry of dl-Neocycloheximide, A New Isomer of Cycloheximide. Tetrahedron Letters 1962, 1167.
Johnson, F., and N. A. StarxovsxY: Glutarimide Antibiotics. Part Iii. The Determination of the Stereochemistry of the Methyl Groups of Cycloheximide Isomers by Nuclear Magnetic Resonance Spectroscopy. Tetrahedron Letters 1962, 1173.
JoHNsoN, F., N. A. Starkovsky and A. A. Carlson: Glutarimide Antibiotics. IN. “Che Stereochemistry of the Dihydrocycloheximides and the Configuration of the Hydroxyl Group of Cycloheximide. J. Amer. Chem. Soc. 87, 4612 (1965).
JoHNsoN, F., N. A. StarxovsxY and VV. D. GrRowIT2: Glutarimide Antibiotics. Part Vii. The Synthesis of dl-Neocycloheximide and the Determination of the Cyclohexanone Ring Stereochemistry of Cycloheximide, its Isomers, and Inactone. J. Amer. Chem. Soc. 87, 3492 (1965).
Johnson, F., N. A. StarxovsxY, A. C. Paton and A. A. C,Arlson: Glutarimide Antibiotics. Part VI. The Total Synthesis of dl-and 1-Cycloheximide. J. Amer. Chem. Soc. 86, 118 (1964).
Johnson, F., N. A. StarxovsxY, A. C. Paton and A. A. C,Arlson: The Total Synthesis of Cycloheximide. J. Amer. Chem. Soc. 88, 149 (1q66).
Johnson, F., and A. Whiteheao: The Stereochemistry of 2-Substituted Cyclohexanone ‘Illumines and the Corresponding Schiffs Bases. Tetrahedron Letters 1964, 3825.
Kharatyan, S., M. Pu`LA, T. Spi2EK, L. DoLczrxov_i and Z. A’ANÉx: Biogenesis of Cycloheximide and Related Compounds. Chem. and Ind. 1963, 1038.
Kohberger, D. L., M. W. Fisher, M. M. Galbraith, A. B. Hillegas, P. L. ThotitrsoN and J. Erlich: Biological Studies of Streptimidone a New Antibiotic. Antibiotics and Chemotherapy 10, 9 (1960).
IìoRisfeld, E. C., and R. G. JoNEs: The Structure of Actidione, An Antibiotic from Streptomyces griseus. Science io8, 437 (1948).
KornrEld, E. C., R. G. JoNEs and T. V. Parke: The Structure and Chemistry of Actidione, An Antibiotic from Streptomyces griseus. J. Amer. Chem. Soc. 71, 150 (1949).
Lawes, B. C.: The Synthesis of Anhydroactidione. J. Amer. Chem. Soc. 82, 6413 (196o).
Lawes, B. C.: Absolute Configuration of Cycloheximide from Thermal Degradation. Abstracts of the 139th Meeting American Chemical Society, St. Louis, Mo., March 1g61, p. 33N.
Lawes, B. C.: Absolute Configuration of Cycloheximide from Thermal Degradation. J. Amer. Chem. Soc. 84, 239 (1962).
Leach, B. E., J. H. Ford and A. J. Whiffex: Actidione au Antibiotic from Streptomyces griseus. J. Amer. Chem. Soc. 69, 474 (1947)
Lemieux, R. A., R. K. Kullig, H. J. Bernstein and W. G. Schneider: Configurational Effects on the Proton Magnetic Resonance Spectra of Six-Membered Ring Compounds. J. Amer. Chem. Soc. 8o, 6098 (r958). 6o. Lemix, A. J.: Chemical Process. United States Patent 2,903, 458 (1959).
Lenin, A. J., and J. H. Ford: lsocycloheximide. J. Organ. Chem. (U.S.A.) 25, 344 (1960).
Loefer, J. B., and T. S. Matney: Growth Inhibition of Free-Living Protozoa by Actidione. Physiol. Zoö1. 25, 272 (1952).
Mc Lure, T. T.: Experiences with Cherry Sprays in 1951. Phytopathology 42, 14 (1952).
Mole, T.: Thermal Retro-aldol Reaction. Chem. and Ind. 196o, 1164.
Notari, R. E., and S. M. Caiola: Catalysis of Streptovitacin-A Dehydration. Kinetics and Mechanisms. J. Pharm. Sci. 58, 1203 (1969).
Okuda, T.: Some Configurational Aspects of Naramycin-A (Cycloheximide) and its Stereoisomerie Antibiotic, Naramycin-B. Chem. Phann. Bull. (Tokyo) 7, 137 (1959).
Okuda, T.: Further Studies on the Absolute Configuration of Naramycin-A (Cycloheximide) and its Isomeric Naramycin-B. Chem. Pharm. Bull. (Tokyo) 7, 259 (1959)•
Okuda, T.: Studies on Streptomyces Antibiotic Cycloheximide. IV. Some Observations on Stereochemical Configurations of Naramycin-A (Cycloheximide) and Naramycin-B. Chem. Pharm. Bull. (Tokyo) 7,659 (1959).
Okuda, T.: Studies on Streptomyces Antibiotic Cycloheximide. V. Synthesis and Stereochemistry of Deoxycycloheximide. Chem. Pharm. Bull (Tokyo) 7, 666 (1959)
Okuda, T.: Studies on Streptomyces Antibiotic, Cycloheximide. VI. The Absolute Configuration of Naramycin-A (Cycloheximide) and its Isomeric Naramycin-B. Chem. Pharm. Bull. (Tokyo) 7,671 (1959).
OxUda, T., K. Ashino, Y. Egawa and M. SuzuKI: The Streptomyces Antibiotic Cycloheximide I. Isolation of Naramycin-A and its Identity with Cycloheximide. Chem. Pharm. Bull. (Tokyo) 6, 711 (1958).
OxuDA, T., and M. Suzuki: Absolute Configuration of Cycloheximide. Chem. Pharm. Bull. (Tokyo) 9, 1014 (1961).
OxuDA, T., and M. Suzuki: Cycloheximide (Naramycin) Part I-I. Yakugaku Kenkyu 33, 371 (1961).
Okuda, T., M. Suzuki and Y. Egawa: Studies on Streptomyces Antibiotic, Cycloheximide. Vii. On the Configuration of Naramycin-B and Isocycloheximide. Chem. Pharm. Bull. (Tokyo) 8, 336 (196o).
Okuda, T., M. Suzuki Synthesis of Cycloheximide Isomers Including Isocycloheximide. J. Antibiotics (Japan), Ser. A 14, 158 (rg61).
Okuda, T., M. Suzuki, Y. Egawa and K. Ashino: Studies on Cycloheximide and its New Stereoisomeric Antibiotic. Chem. Pharm. Bull. (Tokyo) 6, 328 (1958).
Okuda, T., M. Suzuki, Y. Egawa and K. Ashino: Studies on Streptomyces Antibiotic Cycloheximide. 11. Naramycin-B an Isomer of Cycloheximide. Chem. Pharm. Bull. (Tokyo) 7, 27 (1959).
Okuda, T., M. Suzuki, Y. Egawa and K. Rotera: Studies on Streptomyces Antibiotic, Cycloheximide Xiv. Supplemental Physicochemical Data on Cycloheximide and its Related Compounds. Yakugaku Kenkyu 33, 53o (1961).
Okuda, T., M. Suzuki, T. Furijmai and H. Takahashi: Studies On Streptomyces Antibiotic Cycloheximide. Xviii. Isomerization Study of Cycloheximides and Thermal Degradation of Naramycin-B. Chemical Support of the Proposed Absolute Configuration of Cycloheximides. Chem. Pharm. Bull. (Tokyo) II, 730 (1963).
OsATo, T., Y. Morikubo and H. Umezawa: Production and Extraction of Niromycins, Antiviral Antibiotics. J. Antibiotics (Japan), Ser. A 13, 1r0 (1960).
Osato, T., Y. MoRikuBo, S. Yamazaki, T. Hikiji, K. Yang, M. Kanao, T. Osono and H. Umezawa: Screening Studies of Antiviral Substances Produced by Actinomycetes and New Antiviral Substances, Niromycins. J. Antibiotics (Japan), Ser. A 13, 97 (196o).
Palmer, C., and T. E. Maloney: Preliminary Screening for Potential Algicides. Ohio. J. Sci. 55 i (1955).
Paul, R., and S. Tchelitcheff: Constitution Chimique de l’Inactone. Synthèse Partielle de trois Isomères de]’Actidione. Bull. Soc. Chico. France 1955, 1366.
Pettit, G. R., and A. K. DAs Gupta: Actidione Acetate Nitrogen Mustard. Chem. and Ind. 1962, 1016.
Phillips, D. D., M. A. AcItelli and J. Meinwalu: Actidione. 1. The Synthesis of the Glutarimide Moiety. J. Amer. Chem. Soc. 79, 3517 (1957).
Piatak, D. 31., C. C. Yen and R. V. Kennedy, Jr.: Antineoplastic Research. I. Pyrazole and Pyrimidine Derivatives of Dehydrocycloheximide Analogs. J. Med. Chem. 13, 770 (197o).
Preud’HOMmE, J.,and 31. DusosT: L’Inactone, Nouvelle Substance Voisine de l’Actidione Estraite des Cultures de Streptomyces griseass. Handbook 14th Int. Cong. l’ure and Applied Chem. Zurich 1955 382.
l’dE, M., J. CudlfN, L. Doleblova, M. Aoni)RAcEK, J. SPfZek, Z. Vanek and J. Benes: Origin of Terminal Group in Cycloheximide. antibiotic Advan. Res., Prod. Clin. Use, Proc. Congr. Prague 1964, 582.
PCzA, M., J. CudlfN and Z. Vanek: Diversity of Streptimidone and Cycloheximide Biosynthesis. Folia Microbiol. 13, 533 (1968).
Rao, K. V.: C-73: A Metabolic Product of Streptomyces Albulus. J. Organ. Cheng. (U.S.A.) 25, 661 (196o).
E-73: An Antitumor Substance. Part 111. Sonic Derivatives. Antibiotics and Chemotherapy 12, 123 (1962).
E-73: An Antitumor Substance. Part Il. Structure. J. Organ. Chem. (U.S.A.) 82, 1129 (1960).
RAo, K. V., and AV. P. Cullen: E-73: An Antitumor Substance. Part I. Isolation and Characterization. J. Amer. Chem. Soc. 82, 1127 (1960).
Schaeffer, H. J., and V. K. Jais: Determination of the Absolute Configuration of Cycloheximide. J. Pharm. Sci. 5o, 1048 (1961).
Schaeffer, H. J., and V. K. Jain: Synthesis of Dehydrocycloheximide. J. Pharm. Sci. 52, 509 (1963).
Schaeffer, H. J., and V. K. Jain: Investigation of the Stereochemistry of Cycloheximide and its Degrada- tion Products. J. Pharm. Sci. 52, 639 (1963).
Schaeffer, H. J., and V. K. Jain: Investigation of the Stereochemistry of Cycloheximide. J. Pharm. Sci. 53, 144 (1964).
Schaeffer, H. J., and V. K. Jain: The Synthesis of Dehydrocycloheximide and the Conversion of cis2,4-Dimethylcyclohexanone to its trans-Isomer. J. Organ. Chem. (U.S.A.) 29, 2595 (1964).
Shoppee, C. W., F. P. Johnson, R. E. Lack and S. Sternhell: Line Widths of Nuclear Magnetic Resonance Signals Due to Tertiary Methyl Groups. Chem. Comm. 1965, 347.
Siegel, M. R., H. D. Sisler and F. JoHNsoN: The Relationship of Structure to Fungitoxicity of Cycloheximide and Related Glutarimide IJerivatives. Biochem. Pharm. 15, 1213 (1966).
Sisler, H. D., and M. R. Siegel: Cycloheximide and Other Glutarimide Antibiotics. Antibiotics (Mechanism of Action) I, 283 (1967).
Smith, C. G.: Tissue Culture. Bioassay Methods for Streptovitacin-A. Proc. Soc. Exper. Biol. and Med. 100, 747 (i959).
Smith, C. F., W. L. Lumrsis and J. E. Gravy: An Improved Tissue Culture Assay. I. Methodology Studies: Cytotoxicities of Streptovitacins and Cycloheximide. Cancer Research, Sept. 1959.
SoxoLski, W. T., N. J. Filers and G. M. Savage: Paper Chromatography and Microbiological Assay of the Streptovitacins, Antibiotics Annual 1958–1959, New York, Medical Encyclopedia Inc. 1959, 951.
Starkovsky, N. A., A. A. Carlson and F. Johnson: Glutarimide Antibiotics. Xii. A Stereochemical Investigation of the Dehydration Products of Cycloheximide. J. Organ. Chem. (U.S.A.) 31, 2516 (1966).
Starkovsky, N. A., and F. Johnson: Glutarimide Antibiotics. V. The Absolute Configuration of the Side-Chain Asymmetric Center of Cycloheximide. Tetrahedron Letters 1964, 919.
The Nature of Deoxycycloheximide and Epideoxycycloheximide. Tetrahedron Letters 1964, 1015.
Struck, R. F., H. J. Schaeffer, C. A. Krauth, R. J. Kemp, Y. F. Shealy and J. A. Montgomery: Synthesis of Potential Antineoplastic Agents. Xxxiii. ii-Diketone Analogs of the Glutarimide Antibiotics. J. Med. Chem. 7, 646 (1964).
SugawAra, R.: Protomycin, A New Antibiotic of Cycloheximide Group. Ill. Degradation Products. J. Antibiotics (Japan) Ser. A 16, 167 (1963).
Protomycin, A New Antibiotic of the Cycloheximide Group. H. Production and Properties. Antibiotics (Japan) Ser. A 16, 115 (1963).
SugavAra, R., A. Matsumae and T. Rata: Protomycin, A New Antibiotic of Cycloheximide Group. 1. J. Antibiotics (Japan) Ser. A 16, I I I (1963).
Suzuki, M.: Studies on Streptomyces Antibiotic Cycloheximide. Viii. Hvdroxycarbonylation of Optocally Active 2,4-Dimethylcyclohexanone and Chemical Correlation of the Products (I). Chem. Pharm. Bull. (Tokyo) 8, 706 (1960).
Suzuki, M.: Studies on Streptomyces.Antibiotic, Cycloheximide. Viii. Hydroxycarbonylation of Optically Active 2,4-Dimethylcyclohexanone and Chemical Correlation of the Products (2). Chem. Pharm. Bull. (Tokyo) 8, 713 (19(ío).
Suzuki, M.: Studies of Streptomyces Antibiotic, Cycloheximide. IX. Absolute Configuration of Optically Active 2,4-Dimethyl-6-jx-hydroxy(p-substituted-) benzyllcyclohexanones. Chem. Pharm, Bull. (Tokyo) 8, 717 (196o).
Suzuki, M.: Studies on Streptomyces Antibiotic Cycloheximide. XI. Preparation and Chemical Structure of the Oxidation Products (y-Cycloheximides) from Dihydrocycloheximides. Chem. Pharm. Bull. (Tokyo) 9, 778 (196o).
Studies on Streptomyces Antibiotic Cycloheximide. X. Structure-Antimicrobiol Activity Relationship of Cycloheximide and Related Compounds. Yakugaku Zasshi 8o, 1217 (196o).
Suzuki, M., Y. Egawa and T. Okuda: Studies on Streptomyces Antibiotic Cycloheximide. XV. Hydroxycarbonylation of Optically Active 2,4-Dimethylcyclohexanones with Glutarimide-ß-acetaldehyde (Synthesis of Isocycloheximide and its Isomers). Chem. Pharm. Bull. (Tokyo) II, 582 (1963).
Takashita, AL, H. Takahashi and T. Okuda: Studies on Streptomyces Antibiotic, Cycloheximide. Xiii. New Spectrophotometric Determination of Cycloheximide. Chem. Pharm. Bull. (Tokyo) 3o, 304 (1962).
Umezawa, S., and Y. Egawa: Studies of Cycloheximide-Related Compounds. Iii. A Novel Reaction of Aromatic Nitro Ketones with Aldehydes and Secondary Amines. Bull. Chem. Soc. Japan 40, 908 (1967).
VanÉK, Z., M. MA, J. CL’DLÍN, L. Dolezilova and M. Vondr: EK: Metabolites of Streptomyces noursei. Iii. Incorporation of 14C-Carbon Dioxide into Cycloheximide. Biochem. Biophys. Res. Commun. 17, 532 (1964).
VanÉK, Z., M. Puza, J. CudlÍN, M. Vondracek and R. W. Rickards: Metabolites of Streptomyces noursei. X. Biogenesis of Cycloheximide. Folia Microbiol. 14, 388 (1969).
Van Tamelen, E. E., and V. Haarstad: Structure of the Antibiotic Streptimidone. J. Amer. Chem. Soc. 82, 2974 (196o).
Vaughn, J. R.: Cycloheximide, An Antibiotic Effective Against Turf Disease. Phytopathologv 41, 36 (1951).
Velaire, C. D.: Improved Formulation of Cycloheximide Composition and Process for the Control of Blister Rust and Like Fungal Infections in Trees, United States Patent 3,014, 840 (1961).
Welch, J. J.: Rodent Control. A Review of Chemical Repellents for Rodents. J. Agr. Food Chem. 2, 142 (1954)
Wells, H. D., and B. P. Robinson: Cottony Blight of Rye Grass Caused by Pythium aphanidermatum. Phytopathology 44, 509 (1954).
Whiffen, A. J.: The Production, Assay and Antibiotic Activity of Actidione an Antibiotic from Streptomyces griseus. J. Bacteriol. 56, 283 (1948).
The Activity in vitro of Cycloheximide (Actidione) Against Fungi Pathogenic to Plants. Mycologia 42, 253 (195o).
Whiffen, A. J., N. Bohonas and R. L. Emerson: The Production of an Anti-fungal Antibiotic by Streptomyces griseus. J. Bact. 52, 61o (1946).
Williamson, W. R. N.: The Alkylation of Pyrrolidine Enamines. Tetrahedron 3 314 (1958).
WoLinsky, J., and D. Chan: Preparation of (-)-cis-2,4-Dimethvlcyclohexanone from (-1-)-Pulegone. J. Amer. Chem. Soc. 85, 937 (1963).
Woo, P. W. K., H. W. Dion and O. R. Bartz: The Structure of Streptimidone. J. Amer. Chen. Soc. 83, 3085 (1961).
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Johnson, F. (1971). The Chemistry of Glutarimide Antibiotics. In: Herƶ, W., Grisebach, H., Kirby, G.W. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products 29. Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 29. Springer, Vienna. https://doi.org/10.1007/978-3-7091-3259-3_3
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