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Volumn 47, Issue 23, 2008, Pages 4377-4379

Mimicking biosynthesis: Total synthesis of the triterpene natural product abudinol B from a squalene-like precursor

Author keywords

Biomimetic synthesis; Epoxides; Ring closure; Terpenes; Total synthesis

Indexed keywords

ACIDS; BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; CHEMICAL REACTIONS; COMPLEXATION; RAW MATERIALS;

EID: 46749143814     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800749     Document Type: Article
Times cited : (27)

References (29)
  • 8
    • 53549135588 scopus 로고    scopus 로고
    • Several other natural products have also been proposed to arise from squalene tetraepoxide (3), including raspacionins and sodwanones (refs. [3-5]).
    • Several other natural products have also been proposed to arise from squalene tetraepoxide (3), including raspacionins and sodwanones (refs. [3-5]).
  • 10
    • 0001528673 scopus 로고    scopus 로고
    • Preparation and alkylation of imine 7: a J. S. Nowick, R. L. Danheiser, Tetrahedron 1988, 44, 4113;
    • Preparation and alkylation of imine 7: a) J. S. Nowick, R. L. Danheiser, Tetrahedron 1988, 44, 4113;
  • 16
    • 33745700292 scopus 로고    scopus 로고
    • For l-Epoxone, see
    • b) For l-Epoxone, see: M.-X. Zhao, Y. Shi, J. Org. Chem. 2006, 71, 5377.
    • (2006) J. Org. Chem , vol.71 , pp. 5377
    • Zhao, M.-X.1    Shi, Y.2
  • 17
    • 53549127395 scopus 로고    scopus 로고
    • Substrate 10 was unreactive with tert-butyldimethylsilyl triflate (TBSOTf) under a variety of conditions, in contrast with our previous observations with a simpler enolsilane-diepoxide substrate (ref. [7]).
    • Substrate 10 was unreactive with tert-butyldimethylsilyl triflate (TBSOTf) under a variety of conditions, in contrast with our previous observations with a simpler enolsilane-diepoxide substrate (ref. [7]).
  • 23
    • 0000406679 scopus 로고    scopus 로고
    • For representative examples of other transformations in which the epoxide oxygen acts as a nucleophile, see: a F. David, J. Org. Chem. 1981, 46, 3512;
    • For representative examples of other transformations in which the epoxide oxygen acts as a nucleophile, see: a) F. David, J. Org. Chem. 1981, 46, 3512;
  • 29
    • 53549118116 scopus 로고    scopus 로고
    • 2 gave a complicated mixture of products containing neither ent-abudinol (ent-2) nor the by-products 16 or 17.
    • 2 gave a complicated mixture of products containing neither ent-abudinol (ent-2) nor the by-products 16 or 17.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.