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

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Abstract

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.

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Honda, T., Endo, K., & Ono, S. (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. Chemical and Pharmaceutical Bulletin, 48(10), 1545–1548. https://doi.org/10.1248/cpb.48.1545

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