Asymmetric total synthesis of (-)-panacene and correction of its relative configuration |
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Authors: | Boukouvalas John Pouliot Martin Robichaud Joël MacNeil Stephen Snieckus Victor |
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Institution: | Département de Chimie, Université Laval, Quebec City, Quebec G1K 7P4, Canada. john.boukouvalas@chm.ulaval.ca |
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Abstract: | reaction: see text] The first synthesis of (-)-panacene has been accomplished in concise, highly stereoselective fashion from commercially available 2-methoxy-6-methylbenzoic acid (15 steps, 8.3% overall yield). The synthesis unambiguously establishes the correct relative and absolute configuration of panacene, and demonstrates the serviceability of Pd(II)-mediated tandem intramolecular alkoxycarbonylation-lactonization for the expedient assembly of its tricyclic core, and the dual role of asymmetric alkynylation as an initial source of chirality and as a powerful tool for manipulating diastereoselectivity. |
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