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DOI: 10.1055/s-0029-1219236
Stereoselective Total Synthesis of Cladospolide A
Publication History
Publication Date:
20 January 2010 (online)
Abstract
A simple and highly efficient stereoselective total synthesis of cladospolide A, a polyketide natural product, has been achieved. The synthesis involves stereoselective zinc-mediated allylation, pivotal aldol coupling, and ring-closing metathesis. The pivotal aldol coupling is used for the first time for macrolide construction and provides an effective alternative to Yamaguchi macrolactonization.
Key words
stereoselective synthesis - zinc mediator - allylations - aldol coupling - ring-closing metathesis
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References
Acetyl fragment 16 was synthesized (Scheme [³] ) from commercially available epoxide 15, which was subjected to copper(I) cyanide promoted regioselective nucleophilic ring opening with allylmagnesium chloride to provide the corresponding alcohol in 87% yield; acetylation of the alcohol by use of acetic anhydride and pyridine yielded 16.