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Volumn 65, Issue 19, 2000, Pages 6073-6081

A synthesis of C(16),C(18)-bis-epi-cytochalasin D via reformatsky cyclization

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE; CYTOCHALASIN D; DIMETHYLDIOXIRANE; SELENIUM DERIVATIVE; VINYL DERIVATIVE;

EID: 0034703411     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000533q     Document Type: Article
Times cited : (30)

References (38)
  • 2
    • 0346126404 scopus 로고
    • Pendse, G. S., Ed.; Chapman-Hall: New York, Chapter 2
    • Tannenbaum, S. W., Ed. Cytochalasins: Biochemical and Cell Biological Aspects; North-Holland, Amsterdam, 1978. Kapadi, A. H.; Dev, S. In Recent Advances in Cytochalasans; Pendse, G. S., Ed.; Chapman-Hall: New York, 1986; Chapter 2.
    • (1986) Recent Advances in Cytochalasans
    • Kapadi, A.H.1    Dev, S.2
  • 7
    • 0000478322 scopus 로고
    • Stork, G.; Nakahara, Y.; Nakahara, Y.; Greenlee, W. J. J. Am. Chem. Soc. 1978, 100, 7775. Stork, G.; Nakamura, E. J. Am. Chem. Soc. 1983, 105, 5510.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 5510
    • Stork, G.1    Nakamura, E.2
  • 12
    • 0020789928 scopus 로고
    • Vedejs, E.; Gapinski, D. M. J. Am. Chem. Soc. 1983, 105, 5058. Vedejs, E.; Dent, W. H., III; Gapinski, D. M.; McClure, C. K. J. Am. Chem. Soc. 1987, 109, 5437.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 5058
    • Vedejs, E.1    Gapinski, D.M.2
  • 24
    • 0343778387 scopus 로고    scopus 로고
    • note
    • An O-silylated analogue of 15 could be prepared, but it proved unsuitable for the intended synthesis because the corresponding derivative of 5 (replace methoxy by tert-butyldimethylsiloxy) undergoes facile silatropic rearrangement to an isomeric ketone enol silane under a variety of conditions, including exposure to silica gel.
  • 30
    • 0342473273 scopus 로고    scopus 로고
    • The NMR signals of 29 slowly appeared if purified 6 was heated to 85 °C for several hours
    • The NMR signals of 29 slowly appeared if purified 6 was heated to 85 °C for several hours.
  • 34
    • 0001574139 scopus 로고
    • Rubottom, G. M.; Marrero, R. J. Org. Chem. 1975, 40, 3783; Rubottom, G. M.; Gruber, J. M. J. Org. Chem. 1978, 43, 1599.
    • (1975) J. Org. Chem. , vol.40 , pp. 3783
    • Rubottom, G.M.1    Marrero, R.2
  • 35
  • 38
    • 0342907632 scopus 로고    scopus 로고
    • note
    • Irradiation of the C(18) methyl group in 34 gave a strong NOE enhancement of the C(20) vinylic hydrogen, while the corresponding experiment with a sample enriched in 35 resulted in the enhancement of the C(19) hydrogen signal. This evidence is consistent with an extended conformation of the 11-membered ring where the C(18) methyl is pseudoaxial in 34, but pseudoequatorial in 35, and could have been interpreted to make the correct assignment of C(18) configuration.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.