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

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.

SUBMITTER: Venukadasula PK

PROVIDER: S-EPMC2888003 | biostudies-other | 2010 Apr

REPOSITORIES: biostudies-other

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

Venukadasula Phanindra K M PK Chegondi Rambabu R Maitra Soma S Hanson Paul R PR

Organic letters 20100401 7

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. ...[more]

PMID: 20196547

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