Chem. Pharm. Bull., 48(10),1545-1548, October 2000

Construction of an Enantiomerically Pure 6-Substituted 3,5-syn-Dihydroxyhexanoic Acid System by an Enantioselective Deprotonation Strategy: Formal Synthesis of an Antiobesity Agent, (-)-Tetrahydrolipstatin

Toshio HONDA,^* Katsunori ENDO, and Satoko ONO

Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan.

Preparation of 6-substituted 4-hydroxytetrahydro-2H-pyran-2-one (12), a key intermediate for the synthesis of (-)-tetrahydrolipstatin, was achieved in an optically pure form by employing an enantioselective deprotonation reaction of the prochiral bicyclic derivative (5) as a key step.

Key words enantioselective deprotonation; 3,5-O-benzylidenecyclohexanone; chiral base; (-)-tetrahydrolipstatin; antiobesity agent