The Total Synthesis of (–)-Tetrahydrolipstatin

Jennifer A. Bodkin, Edward J. Humphries and Malcolm D. McLeod

Abstract

Careful control during the bromolactonization of β,γ;-unsaturated acid (4) was required to regioselectively afford the trans-β-lactone (3) as the major diastereomer. Radical debromination of (3) followed by a three-step sequence of reactions afforded the lipase inhibitor (–)-tetrahydrolipstatin (1).

Australian Journal of Chemistry 56(8) 795 - 803 (2003) doi:10.1071/CH03121