A Concise, Phosphate-Mediated Approach to the Total Synthesis of (-)-Tetrahydrolipstatin

作者:Venukadasula Phanindra K M; Chegondi Rambabu; Maitra Soma; Hanson Paul R*
来源:Organic Letters, 2010, 12(7): 1556-1559.
DOI:10.1021/ol1002913

摘要

An efficient synthesis of (-)-tetrahydrolipstatin (THL) is reported. This method takes advantage of a phosphate tether-mediated, one-pot, sequential RCM/CM/hydrogenation protocol to deliver THL in eight total steps from a readily prepared (S,S)-triene. The strategy incorporates selective cross-metathesis, regioselective hydrogenation, regio- and diastereoselective cuprate addition, and Mitsunobu Inversion for installation of the C5 formamide ester subunit.