Formal Enantioselective Synthesis of Aplykurodinone-1

Authors


  • We are grateful to the Région Haute-Normandie for generous support and to Morgan Cormier for valuable technical assistance. Helpful discussions with Prof. H. Kotsuki (Kochi University, Japan) are acknowledged. Dedicated to Prof. K. Shishido on the occasion of the 2013 Award of the Pharmaceutical Society of Japan.

Abstract

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Step economy and simplicity were combined in the asymmetric formal synthesis of aplykurodinone-1 (see scheme; TBS=tert-butyldimethylsilyl). The key features of the strategy involve a one-pot aerobic and directed oxidation/deoxygenation and a late-stage controlled epimerization to form the chiral architecture of the molecule.

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