Organic Letters 2004-06-24

Total synthesis of natural (+)-(2's,3'r)-zoapatanol.

Catherine Taillier, Véronique Bellosta, Janine Cossy

Index: Org. Lett. 6(13) , 2149-51, (2004)

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Abstract

[reaction: see text] (+)-Zoapatanol was synthesized by using four key-steps: a Suzuki cross-coupling to prepare a (Z)-alpha,beta-unsaturated ester followed by an enantioselective dihydroxylation to control the C2' and C3' stereocenters, an intramolecular Horner-Wadsworth-Emmons olefination to construct the oxepane ring, and a chemoselective nucleophilic addition/Birch reduction process of a Weinreb amide to introduce simultaneously the beta,gamma-unsaturated ketone on the side-chain and regenerate alcohols from benzyl ethers.