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Volumn 42, Issue 29, 2003, Pages 3406-3409

Stereospecific total synthesis of the antiviral agent hamigeran B - Use of large silyl groups to enforce facial selectivity and to suppress hydrogenolysis

Author keywords

Hamigeran B; Hydrogenolysis; Natural products; Silyl groups; Total synthesis

Indexed keywords

CHEMICAL BONDS; HYDROGENATION; STEREOCHEMISTRY; VIRUSES;

EID: 0042530467     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351519     Document Type: Article
Times cited : (44)

References (24)
  • 3
    • 0035476435 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 3675-3678;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3675-3678
  • 5
    • 0035476828 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 3679-3683.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3679-3683
  • 6
    • 12444257127 scopus 로고    scopus 로고
    • unpublished observations
    • J. Wang, unpublished observations.
    • Wang, J.1
  • 9
    • 0002519349 scopus 로고
    • c) Examples of hydrogenation of tetrasubstituted double bonds conjugated with benzene rings are known (Beilstein database); see, especially: A. C. G. Gray, H. Hart, J. Am. Chem. Soc. 1968, 90, 2569-2578.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 2569-2578
    • Gray, A.C.G.1    Hart, H.2
  • 13
    • 12444252694 scopus 로고    scopus 로고
    • note
    • Another stereoisomer was formed for which no NOE was observed between H5 and the methyl group at C9.
  • 14
    • 12444268063 scopus 로고    scopus 로고
    • note
    • Based on observation of NOE effects.
  • 16
    • 12444331726 scopus 로고    scopus 로고
    • note
    • It is believed that hydrogenolysis is facilitated by development of a partial positive charge on the benzylic carbon (see ref. [10]); siloxy groups are not as effective at stabilizing an adjacent positive charge as alkoxy groups (see ref. [12]).
  • 21
    • 12444300905 scopus 로고    scopus 로고
    • note
    • Examples of the following have been reported (without comment): A benzylic tert-butyldimethylsilyl ether survives hydrogenation of disubstituted (e.g. ref. [16]) and trisubstituted (ref. [2a]) double bonds. A tertiary benzylic trimethylsilyl ether survives hydrogenation of a tetrasubstituted double bond (ref. [17]).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.