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Volumn 37, Issue 19, 1996, Pages 3291-3294

Synthetic studies on the rhizoxins. II. An approach to the C10-C26 subunit using "substrate directed" allylstannane additions to aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

RHIZOXIN;

EID: 0029937762     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00578-3     Document Type: Article
Times cited : (29)

References (34)
  • 5
    • 0038981679 scopus 로고
    • Society for Industrial Microbiology. Demain, G. A.; Somkuti, Hunter-Cevera, J. C.; Rossmoore, H. W. Ed. Chapter 10
    • c) Iwasaki, S. Novel Microbial Products for Medicine and Agriculture, Society for Industrial Microbiology. Demain, G. A.; Somkuti, Hunter-Cevera, J. C.; Rossmoore, H. W. Ed. 1989, Chapter 10; page 79.
    • (1989) Novel Microbial Products for Medicine and Agriculture , pp. 79
    • Iwasaki, S.1
  • 19
    • 85029982642 scopus 로고    scopus 로고
    • note
    • 2) did not promote reaction at all; with 2.0 equiv. reaction was observed, but without significant stereoselectivity. It seems likely that the first equivalent of Lewis acid is irreversibly sequestered by formation of a 5-ring chelate between the benzyl and methyl ethers in this case, thus preventing the desired chelation between the aldehyde oxygen and the methyl ether moieties. Use of the TBS silyl ether precludes the undesired sense of complexation.
  • 23
    • 85029985529 scopus 로고    scopus 로고
    • note
    • 3 substituent is due to allylic strain.
  • 26
    • 0001218374 scopus 로고
    • For descriptions of "chelation" vs "non-chelation" controlled reactions and 1,3 asymmetric induction, see: a) Reetz, M. T.; Harms, K.; Reif, W. Tetrahedron Lett. 1988, 29, 5881.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5881
    • Reetz, M.T.1    Harms, K.2    Reif, W.3
  • 34
    • 85029991031 scopus 로고    scopus 로고
    • note
    • 13C NMR; 160.9, 159.1, 140.5, 138.7, 137.2, 137.0, 135.9, 131.1, 129.3, 124.2, 120.2, 114.4, 113.7, 96.8, 88.7, 79.5, 76.5, 70.7, 56.3, 55.6, 55.3, 53.4, 41.1, 37.5, 32.3, 14.8, 14.4, 13.9, 12.1, 10.0.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.