Formal enantioselective synthesis of (+)-compactin |
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Authors: | Robichaud Joël Tremblay François |
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Institution: | Merck Frosst Canada Ltd., 16711 Trans Canada Highway, Kirkland, Québec H9H 3L1, Canada. joel_robichaud@merck.com |
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Abstract: | reaction: see text] The challenging structural features and important biological activity of (+)-compactin (1) explain the substantial synthetic interest that it has generated. We report a novel enantioselective approach to the advanced intermediate 2a, which constitutes a formal synthesis of (+)-1. The sequence utilizes MacMillan's organocatalytic Mukaiyama-Michael reaction, which stereoselectively adds the silyloxyfuran 6 to alpha,beta-unsaturated aldehyde 7. The chirality generated in this reaction guides the formation of the other three consecutive stereocenters found in 2a. |
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