(+)-Zwittermicin A. Rapid Assembly of C9−C15 and a Formal Total Synthesis

A short, enantioselective synthesis of the C9−C15 portion of (+)-zwittermicin A is reported that exploits directional functionalization of the known hepta-2,5-diyne-1,7-diol by partial reduction of the two triple bonds followed by Sharpless asymmetric epoxidation and boron-directed double ring-openi...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-10, Vol.74 (20), p.7660-7664
Main Authors: Rogers, Evan W, Molinski, Tadeusz F
Format: Article
Language:English
Subjects:
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
Stereoisomerism
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Summary:A short, enantioselective synthesis of the C9−C15 portion of (+)-zwittermicin A is reported that exploits directional functionalization of the known hepta-2,5-diyne-1,7-diol by partial reduction of the two triple bonds followed by Sharpless asymmetric epoxidation and boron-directed double ring-opening with sodium azide under Miyashita conditions. Subsequent desymmetrization of the C 2-symmetric diazidotetraol product converges upon (−)-3the enantiomer of the key intermediate of our earlier structural proof and synthesis of (−)-zwittermicin Aand constitutes a formal synthesis of (+)-zwitttermicin A.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo901007v