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

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

doi:10.1021/0l1002913

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 journal › Article › peer-review

40 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 language	English (US)
Pages (from-to)	1556-1559
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	7
DOIs	https://doi.org/10.1021/0l1002913
State	Published - Apr 2 2010
Externally published	Yes

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

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.",

author = "Venukadasula, {Phanindra K.M.} and Rambabu Chegondi and Soma Maitra and Hanson, {Paul R.}",

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T1 - A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin

AU - Venukadasula, Phanindra K.M.

AU - Chegondi, Rambabu

AU - Maitra, Soma

AU - Hanson, Paul R.

PY - 2010/4/2

Y1 - 2010/4/2

N2 - (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.

AB - (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.

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JO - Organic Letters

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

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