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Volumn 45, Issue 35, 2006, Pages 5832-5837

Studies on iejimalide B: Preparation of the seco acid and identification of the molecule's "Achilles Heel"

Author keywords

Heck reaction; Lactones; Macrolides; Olefination; Total synthesis

Indexed keywords

CARBOXYLIC ACIDS; ESTERIFICATION; ESTERS; OLEFINS; SYNTHESIS (CHEMICAL);

EID: 33748574304     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601859     Document Type: Article
Times cited : (42)

References (48)
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    • The activity data are available from the NCI homepage (http://www.dtp.nci.nih.gov/docs/dtp_search.html).
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    • Although the NCl data show no particular selectivity, a preliminary report from the Walther Cancer Research Center (http://www.nd.edu/≈science/ documents/waltherbrochure.pdf) claims spectacular effects against colon cancer and stunning morphological changes upon injection of iejimalides into solid tumors.
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    • note
    • For details see the Supporting Information.
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    • c) for a recent application from this research group see: A. Fürstner, P. Hannen, Chem. Eur. J. 2006, 12, 3006-3019.
    • (2006) Chem. Eur. J. , vol.12 , pp. 3006-3019
    • Fürstner, A.1    Hannen, P.2
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    • note
    • The use of TBAF and other fluoride sources scrambled the trisubstituted olefin of the enoate.
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    • see. Ref. [24]
    • Note that an alcohol might interfere with the Smiles rearrangement, which constitutes the crucial second step of the Kocienski variant of the Julia olefination, see. Ref. [24].
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    • note
    • Attempts to suppress this pathway by replacement of DMAP with 2,6-di-tert-butylpyridine as a more bulky base were unsuccessful.
  • 44
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    • Formation of phenols by electrocyclizations of polyunsaturated ketenes: a) M. J. Heileman, H. W. Moore, Tetrahedron Lett. 1998, 39, 3643-3646;
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3643-3646
    • Heileman, M.J.1    Moore, H.W.2
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    • Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3012-3043


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.