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A Concise, Phosphate-Mediated Approach to the Total Synthesis of (−)-Tetrahydrolipstatin
Venukadasula, Phanindra K. M. Chegondi, Rambabu Maitra, Soma Hanson, Paul R.
Venukadasula, Phanindra K. M.
Chegondi, Rambabu
Maitra, Soma
Hanson, Paul R.
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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.
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2010-04
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American Chemical Society
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Venukadasula_2010.pdf
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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