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Volumn 39, Issue 9, 2000, Pages 1664-1666

The synthesis of streptogramin antibiotics: (-)-Griseoviridin and its C- 8 Epimer

Author keywords

Antibiotics; Macrolides; Metathesis; Natural products; Total synthesis

Indexed keywords

GRISEOVIRIDIN; STREPTOGRAMIN DERIVATIVE; UNCLASSIFIED DRUG; VIRGINIAMYCIN;

EID: 0034595258     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000502)39:9<1664::AID-ANIE1664>3.0.CO;2-#     Document Type: Article
Times cited : (132)

References (27)
  • 1
    • 0003334991 scopus 로고
    • The Streptogramin Family of Antibiotics
    • (Eds.: J. W. Corcoran, F. H. Hahn), Springer, New York
    • a) "The Streptogramin Family of Antibiotics", D. Vasquez in Antibiotics III (Eds.: J. W. Corcoran, F. H. Hahn), Springer, New York, 1975;
    • (1975) Antibiotics III
    • Vasquez, D.1
  • 6
    • 1642624022 scopus 로고    scopus 로고
    • Sept. 22
    • Denver Rocky Mountain News, Sept. 22, 1999: "FDA approved Synercid to treat vancomycin-resistant enterococcal and Staph infections". Synercid is a trade name for the combination of Group A and B streptogramins manufactured by Rhone-Poulene Rorer.
    • (1999) Denver Rocky Mountain News
  • 14
    • 0017242119 scopus 로고
    • B. W. Bycroft, T. J. King, J. Chem. Soc. Perkin Trans. 1 1976, 1996. Professor Bycroft informed us after the appearance of his paper that the configuration at C-18 was R rather than S and we confirmed this by inserting the atomic coordinates obtained by the British group into the SHELXTL program, version 5, which showed that both hydroxy groups at C-18 and C-20 were indeed syn as shown in 1.
    • (1976) J. Chem. Soc. Perkin Trans. 1 , pp. 1996
    • Bycroft, B.W.1    King, T.J.2
  • 15
    • 0018855575 scopus 로고
    • Another version of this lactone 5 was prepared 20 years ago by a slightly different procedure. However the benzamide and methyl ester in 5 proved to be worthless in proceeding with the synthesis of griseoviridin. A. I. Meyers, R. A. Amos, J. Am. Chem. Soc. 1980, 102, 870.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 870
    • Meyers, A.I.1    Amos, R.A.2
  • 19
    • 0012615648 scopus 로고    scopus 로고
    • 1H NMR spectrum with that of the C-Me diastereomeric lactone prepared by cyclization under Yamamoto lactonization conditions; see: K. Ishihara, M. Kubota, A. Kurihara, H. Yamamoto, J. Org. Chem. 1996, 61, 4560.
    • (1996) J. Org. Chem. , vol.61 , pp. 4560
    • Ishihara, K.1    Kubota, M.2    Kurihara, A.3    Yamamoto, H.4
  • 21
    • 0001515436 scopus 로고
    • and references therein
    • P. K. Sonnet, Tetrahedron 1980, 36, 557, and references therein.
    • (1980) Tetrahedron , vol.36 , pp. 557
    • Sonnet, P.K.1
  • 25
    • 0032580376 scopus 로고    scopus 로고
    • and references therein
    • R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413, and references therein.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 26
    • 85007641549 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum.
  • 27
    • 85007632677 scopus 로고    scopus 로고
    • note
    • A sample of the heretofore unknown C-8 epi-griseoviridin has been submitted for antibacterial screening (Aventis) and found to be only very poorly active (courtesy of Dr. S. Dutka-Malen).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.