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

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

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Issue Date

2010-04

Author

Venukadasula, Phanindra K. M.

Chegondi, Rambabu

Maitra, Soma

Hanson, Paul R.

Publisher

American Chemical Society

Type

Article

Article Version

Scholarly/refereed, author accepted manuscript

Rights

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol1002913

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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 8 total steps from a readily prepared (S,S)-triene. The strategy incorporates selective cross metathesis, regio-selective hydrogenation, regio- and diastereoselective cuprate addition and Mitsunobu inversion for installation of the C5 formamide ester subunit.

Citation

Venukadasula, P. K. M., Chegondi, R., Maitra, S., & Hanson, P. R. (2010). A Concise, Phosphate-Mediated Approach to the Total Synthesis of (−)-Tetrahydrolipstatin. Organic Letters, 12(7), 1556–1559. http://doi.org/10.1021/ol1002913

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