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

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

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

(Figure Represented) 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.

Original languageEnglish (US)
Pages (from-to)1556-1559
Number of pages4
JournalOrganic Letters
Volume12
Issue number7
DOIs
StatePublished - Apr 2 2010
Externally publishedYes

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