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Volumn 69, Issue 7, 2004, Pages 2569-2572

Unified Synthesis of C19-C26 Subunits of Amphidinolides B1, B2, and B3 by Exploiting Unexpected Stereochemical Differences in Crimmins' and Evans' Aldol Reactions

Author keywords

[No Author keywords available]

Indexed keywords

BORON; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 1842503791     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035829l     Document Type: Article
Times cited : (53)

References (51)
  • 22
    • 0032483753 scopus 로고    scopus 로고
    • For total syntheses of other members of the amphidinolides: (a) Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198-99.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 11198-11199
    • Williams, D.R.1    Kissel, W.S.2
  • 38
    • 1842580170 scopus 로고    scopus 로고
    • note
    • 25 versus the target 11; however, the alkylation of the enantiomeric (S)-propylene oxide proceeds in poor selectivity due to its mismatched relationship to the approaching enolate. This stereocenter will be inverted later in the synthetic sequence.
  • 41
    • 1842475523 scopus 로고    scopus 로고
    • note
    • 4 immediately prior to addition of the aldehyde. See ref 14.
  • 47
    • 0037182708 scopus 로고    scopus 로고
    • The preference for a boat transition state in oxazolidinethione aldol reactions has been proposed previously. (a) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253-56.
    • (2002) Org. Lett. , vol.4 , pp. 2253-2256
    • Guz, N.R.1    Phillips, A.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.