Abstract
An efficient and practical total synthesis of (+)-gonio-thalesdiol and its 2,5- EPI analogue is described herein. The key -features include a diastereoselective reduction of C-5 keto with Zn(BH 4 ) 2 to generate the desired stereochemistry at C-5. The tetra-hydrofuran backbone of natural goniothalesdiol was synthesized under basic conditions via epoxide formation, followed by in situ 5- EXO opening of the epoxide ring with γ-benzoyloxy oxygen upon -debenzoylation. For the 2,5- EPI analogue, the tetrahydrofuran ring was formed via acid-catalyzed acetonide deprotection followed by concomitant S N 2 displacement of the O-mesyl group at C-5 center with C-2-γ-oxygen.
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