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Volumn 69, Issue 8, 2004, Pages 2797-2804

A New Stereoselective Synthesis of Ciguatoxin Right Wing Fragments

Author keywords

[No Author keywords available]

Indexed keywords

BIOMEDICAL ENGINEERING; OLEFINS; REDUCTION; STEREOCHEMISTRY;

EID: 1842739309     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049877x     Document Type: Article
Times cited : (50)

References (80)
  • 1
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    • For recent reviews, see: (a) Scheuer, P. J. Tetrahedron 1994, 50, 3-18.
    • (1994) Tetrahedron , vol.50 , pp. 3-18
    • Scheuer, P.J.1
  • 2
    • 0035239230 scopus 로고    scopus 로고
    • (b) Lewis, R. J. Toxicon 2001, 39, 97-106.
    • (2001) Toxicon , vol.39 , pp. 97-106
    • Lewis, R.J.1
  • 18
    • 1642320896 scopus 로고    scopus 로고
    • For an account of the total synthesis of CTX3C, see: Inoue, M.; Hirama, M. Synlett 2004, 577-595.
    • (2004) Synlett , pp. 577-595
    • Inoue, M.1    Hirama, M.2
  • 24
    • 0034246704 scopus 로고    scopus 로고
    • (c) Yet, L. Chem. Rev. 2000, 100, 2963-3007.
    • (2000) Chem. Rev. , vol.100 , pp. 2963-3007
    • Yet, L.1
  • 49
    • 85039525070 scopus 로고    scopus 로고
    • note
    • The numbering of carbon atoms in all compounds in this paper corresponds to that of CTX3C.
  • 53
    • 85077634689 scopus 로고
    • For reviews on Mitusnobu reaction, see: (a) Mitsunobu, O. Synthesis 1981, 1-28.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 67
  • 70
    • 0033534698 scopus 로고    scopus 로고
    • We also attempted the 1,2-hydride shift of epoxide i using various Lewis acids directly to obtain ii. However, only 6,6-spiroacetal iii was observed as a major product, which arose from the nucleophilic attack of C46-oxygen and concomitant loss of the MOM group. For a successful application of the related 1,2-hydride shift, see: Bazin, H. G.; Wolff, M. W.; Linhardt, R. J. J. Org. Chem. 1999, 64, 144-152. (chemical equation presented)
    • (1999) J. Org. Chem. , vol.64 , pp. 144-152
    • Bazin, H.G.1    Wolff, M.W.2    Linhardt, R.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.