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Literature DB >> 20196547

A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin.

Phanindra K M Venukadasula¹, Rambabu Chegondi, Soma Maitra, Paul R Hanson.

Abstract

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.

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Year: 2010 PMID： 20196547 PMCID： PMC2888003 DOI： 10.1021/ol1002913

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

33 in total

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