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Asymmetric Total Synthesis of (−)-Panacene and Correction of Its Relative Configuration

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https://figshare.com/articles/dataset/Asymmetric_Total_Synthesis_of_Panacene_and_Correction_of_Its_Relative_Configuration/3067135
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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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2016-03-01
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