First stereoselective total synthesis of brevipolide M

The first stereoselective total synthesis of a cytotoxic brevipolide M, which shares a pyrone framework bearing a tetrahydrofuran moiety and a cinnamate group with the readily available (-)-DET, is described. The key steps involved in the synthesis are the epoxide-opening, Brown's allylation, a...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017-08, Vol.15 (30), p.6393-6400
Main Authors: Shiva Raju, Kasa, Sabitha, Gowravaram
Format: Article
Language:English
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Summary:The first stereoselective total synthesis of a cytotoxic brevipolide M, which shares a pyrone framework bearing a tetrahydrofuran moiety and a cinnamate group with the readily available (-)-DET, is described. The key steps involved in the synthesis are the epoxide-opening, Brown's allylation, and the RCM reaction to install an α,β-unsaturated lactone ring and the inversion of the C-6' stereogenic hydroxyl group using the Mitsunobu reaction.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01438d