A Novel, Efficient, Diastereo- and Enantioselective Mukaiyama Aldol-Based Synthesis of a Vinyl Cyclopentanone Core Derivative of Viridenomycin

A strategy has been developed for a rapid seven-step construction of a chiral, nonracemic vinyl cyclopentanone building block as part of a synthetic approach to viridenomycin, using a diastereo- and enantioselective Mukaiyama aldol and intramolecular Knoevenagel condensation as key steps.

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Bibliographic Details
Published in:Organic letters 2007-12, Vol.9 (26), p.5565-5568
Main Authors: Batsanov, Andrei S, Knowles, Jonathan P, Lightfoot, Andrew P, Maw, Graham, Thirsk, Carl E, Twiddle, Steven J. R, Whiting, Andrew
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Cyclopentanes - chemistry
Lactams - chemical synthesis
Stereoisomerism
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Summary:A strategy has been developed for a rapid seven-step construction of a chiral, nonracemic vinyl cyclopentanone building block as part of a synthetic approach to viridenomycin, using a diastereo- and enantioselective Mukaiyama aldol and intramolecular Knoevenagel condensation as key steps.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol7025262