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Volumn 125, Issue 1, 2003, Pages 46-47

Total synthesis of gambierol

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKADIENE; ALKENE DERIVATIVE; ALPHA CHLOROACETOXY ETHER; ALUMINUM; BROMOALKENE; CARBOXYLIC ACID; CIGUATOXIN; COPPER; ETHER DERIVATIVE; GAMBEIROL; NATURAL PRODUCT; NEUROTOXIN; PYRIDINE; UNCLASSIFIED DRUG; ZINC;

EID: 0037425560     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028726d     Document Type: Article
Times cited : (124)

References (39)
  • 1
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    • (a) Shimizu, Y. Chem. Rev. 1993, 93, 1685-1698.
    • (1993) Chem. Rev. , vol.93 , pp. 1685-1698
    • Shimizu, Y.1
  • 5
    • 0030944753 scopus 로고    scopus 로고
    • (c) Mori, Y. Chem.-Eur. J. 1997, 3. 849-852. Also see:
    • (1997) Chem.-Eur. J. , vol.3 , pp. 849-852
    • Mori, Y.1
  • 6
    • 0001399218 scopus 로고    scopus 로고
    • (d) Hoberg, J. O. Tetrahedron 1998, 54, 12630-12670.
    • (1998) Tetrahedron , vol.54 , pp. 12630-12670
    • Hoberg, J.O.1
  • 21
    • 0001352339 scopus 로고    scopus 로고
    • During our study, very recently the Sasaki and Tachibana group reported the first total synthesis of 1. (a) Fuwa, H.; Sasaki, M.; Satake, M.; Tachibana, K. Org. Lett. 2002, 4, 2981-2984.
    • (2002) Org. Lett. , vol.4 , pp. 2981-2984
    • Fuwa, H.1    Sasaki, M.2    Satake, M.3    Tachibana, K.4
  • 23
    • 0012371397 scopus 로고    scopus 로고
    • note
    • For the preparation of 3 and 4, see Supporting Information.
  • 26
  • 31
    • 0012456444 scopus 로고    scopus 로고
    • note
    • N2 pathway. The D ring of the desired isomer 2, in which all of the substituents take an equatorial position, is more thermally stable than that of 9. The details of the mechanism are under investigation. We appreciate a referee who pointed out the above problems, and we also thank Professor T. Oishi (Osaka University) and Professor M. Inoue (Tohoku University) for suggesting the use of the chloroacetyl group.
  • 32
    • 0012374134 scopus 로고    scopus 로고
    • note
    • For the determination of the stereochemistries of 2 and 9, see Supporting Information.
  • 38
    • 0026593737 scopus 로고
    • Corey, E. J.; Yi, K. Y. Tetrahedron Lett. 1992, 33, 2289-2290. The other attempts for desilylating the protected gambierol having the triene side chain, for example, the use of TBAF, TAS-F, and SiF4, resulted in failure as reported by Sasaki, see ref 5.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 2289-2290
    • Corey, E.J.1    Yi, K.Y.2
  • 39
    • 0012471867 scopus 로고    scopus 로고
    • note
    • Fuji Silysia silica gel was used for the purification of 1. Although the detail is not clear, the use of Kanto Chemical silica gel (neutral) caused partial isomerization of 1. See Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.