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Volumn , Issue 8, 2009, Pages 1303-1306

Asymmetric total synthesis of (+)-brefeldin A: Intramolecular epoxide-opening/RCM strategy

Author keywords

(+) brefeldin A; Cyclizations; Epoxides; Metathesis; Total synthesis

Indexed keywords

ALLYLSILANE; BREFELDIN A; CYCLOPENTANE; EPOXIDE; LEWIS ACID; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 67649418184     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1216723     Document Type: Article
Times cited : (20)

References (43)
  • 3
    • 44449119617 scopus 로고    scopus 로고
    • For the representative recent syntheses of BFA and related references, see the following references
    • For the representative recent syntheses of BFA and related references, see the following references: (a) Wu, Y.; Gao, J. Org. Lett. 2008, 10, 1533.
    • (2008) Org. Lett. , vol.10 , pp. 1533
    • Wu, Y.1    Gao, J.2
  • 13
    • 0002339617 scopus 로고
    • See also the following pioneering works on brefeldin A synthesis
    • See also the following pioneering works on brefeldin A synthesis: (k) Corey, E. J.; Wollenberg, R. H. Tetrahedron Lett. 1976, 4705.
    • (1976) Tetrahedron Lett. , pp. 4705
    • Corey, E.J.1    Wollenberg, R.H.2
  • 17
    • 1842483218 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see
    • For recent reviews on olefin metathesis, see: (a) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
    • (2004) Chem. Rev. , vol.104 , pp. 1317
    • Diver, S.T.1    Giessert, A.J.2
  • 23
    • 54749129382 scopus 로고    scopus 로고
    • For an asymmetric desymmetrization method, see
    • For an asymmetric desymmetrization method, see: Li, Z.; Zhanh, W.; Yamamoto, H. Angew. Chem. Int. Ed. 2008, 47, 7520.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7520
    • Li, Z.1    Zhanh, W.2    Yamamoto, H.3
  • 32
    • 0001856640 scopus 로고
    • For the synthesis of BFA by intramolecular cyclization reactions using allylsilanes, see: Epoxide opening
    • For the synthesis of BFA by intramolecular cyclization reactions using allylsilanes, see: (a) Epoxide opening: Hatakeyama, S.; Sugawara, K.; Kawamura, M.; Takano, S. Synlett 1990, 691.
    • (1990) Synlett , pp. 691
    • Hatakeyama, S.1    Sugawara, K.2    Kawamura, M.3    Takano, S.4
  • 33
    • 67649423569 scopus 로고    scopus 로고
    • β-Lactone opening: ref 3j
    • (b) β-Lactone opening: ref 3j
  • 42
    • 67649454769 scopus 로고    scopus 로고
    • note
    • We were not able to isolate the minor Z-isomers. Only E-isomers were isolated after column chromatography.
  • 43
    • 67649417279 scopus 로고    scopus 로고
    • note
    • 2O (4:1, 0.1 mL)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.