Total synthesis of (-)-laulimalide |
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Authors: | Wender Paul A Hegde Sayee G Hubbard Robert D Zhang Lei |
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Affiliation: | Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. wenderp@stanford.edu |
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Abstract: | (-)-Laulimalide (1), a structurally novel macrolide isolated in trace amounts from marine sponges, promotes abnormal tubulin polymerization and apoptosis in vitro, with a similar mode of action to that of Taxol(R), but with potentially less susceptibility to multidrug resistance. Herein, a flexible and convergent asymmetric synthesis of (-)-laulimalide is described. This synthesis featured a highly diastereoselective Sakurai reaction of 2 with 3 and a regioselective macrolactonization of an unprotected vicinal diol. Laulimalide was synthesized in 25 steps (longest linear; 36 overall) in 3.5% overall yield, providing a uniquely short and efficient route to 1 and its analogues. |
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