Synthesis and antifungal activity of the four stereoisomers of streptimidone, a glutarimide antibiotic from Streptomyces rimosus forma paromomycinus

European Journal of Organic Chemistry

Volumn , Issue 20, 2000, Pages 3459-3462

  Kondo, Hitoshi ^a   Oritani, Takayuki ^a   Kiyota, Hiromasa ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Aldol reactions; Antibiotics; Glutarimides; Streptimidone; Total synthesis

Indexed keywords

ANTIFUNGAL AGENT; GLUTARIMIDE DERIVATIVE; PROPIONIC ACID DERIVATIVE; STREPTIMIDONE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOISOMERISM; STREPTOMYCES;

EID: 0033755070     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200010)2000:20<3459::AID-EJOC3459>3.0.CO;2-F     Document Type: Article

References (12)

1. [1a] R. P. Frohardt, H. W. Dion, Z. L. Jakubowski, A. Rydeer, J. C. French, O. R. Bartz, J. Am. Chem. Soc. 1959, 81, 5500-5506. -
2. [1b] M. S. Allen, A. M. Decker, R. W. Rickards, Aust. J. Chem. 1976, 29, 673-679.
3. B. S. Kim, S. S. Moon, B. K. Hwang, J. Agric. Food Chem. 1999, 47, 3372-3380.
4. A. M. Becker, R. W. Rickards, Helv. Chim. Acta 1976, 59, 2393-2401.
5. J. H. Ford, W. Klomparens, C. L. Hamner, Plant Dis. Rep. 1958, 42, 680-695.
6. Y. Egawa, M. Suzuki, T. Okuda, Chem. Pharm. Bull. 1963, 11, 589-596.
7. J. Ukai, Y. Ikeda, N. Ikeda, H. Yamamoto, Tetrahedron Lett. 1983, 24, 4029-4033.
8. H. Nagaoka, Y. Kishi, Tetrahedron 1981, 37, 3873-3888.
9. All four diastereomers of 5 have been reported: L. J. Dolby, F. A. Meneghini, T. Koizumi, J. Org. Chem. 1968, 33, 3060-3066.
10. The corresponding (S,S)-6 isomer has been reported: K. Mori, T. Ebata, Tetrahedron 1986, 42, 4413-4420.
11. D. Seebach, V. Ehria, M. Teschner, Liebigs Ann. Chem. 1976, 1357-1369.
12. H. Kondo, T. Oritani, K. Yamashita, Agric. Biol. Chem. 1988, 52, 129-133.