Synthesis of the C21-C34 fragment of antascomicin B

TETRAHEDRON LETTERS

卷:52

Article

Hutchison, John M.¹  Gibson, Andrew S.¹  Williams, David T.¹  McIntosh, Matthias C.¹ 

[1] Univ Arkansas, Fayetteville, AR 72701 USA

关键词: Ireland-Claisen rearrangement;    Allylic diazene rearrangement;    Directed hydrogenation;    Natural product;   

DOI  :  10.1016/j.tetlet.2011.09.027

来源: Elsevier

【 摘 要 】

The C21-C34 fragment of the potent FKBP12-binding macrolide antascomicin B was prepared using Ireland-Claisen and allylic diazene rearrangements to establish the C26/C27 and the C23 stereocenters, respectively. Directed hydrogenation installed the C29 beta-configuration. The fragment possesses 7 of the 11 fixed stereocenters contained in the natural product. (C) 2011 Elsevier Ltd. All rights reserved.

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