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Volumn 22, Issue 5, 2011, Pages 499-505

Enantioselective total synthesis of iso-cladospolide B, cladospolide C and cladospolide B from tartaric acid

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CLADOSPOLIDE B; CLADOSPOLIDE C; ISOCLADOSPOLIDE B; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79955466292     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.02.018     Document Type: Article
Times cited : (20)

References (43)
  • 6
    • 33645459127 scopus 로고    scopus 로고
    • For other syntheses of the structure of iso-cladospolide B see: B.M. Trost, and A. Aponick J. Am. Chem. Soc. 128 2006 3931
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 3931
    • Trost, B.M.1    Aponick, A.2
  • 27
    • 33846245038 scopus 로고    scopus 로고
    • For a general approach to the synthesis of γ-keto amides from tartaric acid see: K.R. Prasad, and A. Chandrakumar Tetrahedron 63 2007 1798
    • (2007) Tetrahedron , vol.63 , pp. 1798
    • Prasad, K.R.1    Chandrakumar, A.2
  • 28
    • 77951132634 scopus 로고    scopus 로고
    • For recent application of γ-keto amides derived from tartaric acid in natural product synthesis see: K.R. Prasad, and A.B. Pawar Synlett 2010 1093
    • (2010) Synlett , pp. 1093
    • Prasad, K.R.1    Pawar, A.B.2
  • 38
    • 79955470747 scopus 로고    scopus 로고
    • In all cross metathesis reactions of 10, with penten-2-ol, the formation of a minor amount of the dimer resulting from dimerization of penten-2-ol was also observed. The E/Z ratio of the product olefin in 11a and 11b is inconclusive from NMR. However, stereochemistry of the olefin is of no consequence as it is saturated in the next step involving hydrogenation
    • In all cross metathesis reactions of 10, with penten-2-ol, the formation of a minor amount of the dimer resulting from dimerization of penten-2-ol was also observed. The E/Z ratio of the product olefin in 11a and 11b is inconclusive from NMR. However, stereochemistry of the olefin is of no consequence as it is saturated in the next step involving hydrogenation.
  • 40
    • 0031682189 scopus 로고    scopus 로고
    • For application of this strategy in the synthesis of allylic alcohols, see: C. Schneider, and U. Kazmaier Synthesis 1998 1314
    • (1998) Synthesis , pp. 1314
    • Schneider, C.1    Kazmaier, U.2
  • 42
    • 0001233216 scopus 로고
    • 1H NMR. For Z-predominant Wittig olefinations with glyceraldehyde acetonide see: N. Minami, S.S. Ko, and Y. Kishi J. Am. Chem. Soc. 104 1982 1109
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 1109
    • Minami, N.1    Ko, S.S.2    Kishi, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.