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

A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin.
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DOI:
10.1021/ol1002913
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发表时间:
2010-04-02
期刊:
影响因子:
5.2
通讯作者:
Hanson, Paul R.
Hanson, Paul R.
中科院分区:
化学1区
文献类型:
--
作者:
Venukadasula, Phanindra K. M.;Chegondi, Rambabu;Maitra, Soma;Hanson, Paul R.

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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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