Journal
TETRAHEDRON
Volume 68, Issue 36, Pages 7280-7287Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.06.104
Keywords
Polyketides; Fungal metabolites; Olefination; 2-Pyrones; Total synthesis
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The total synthesis of the 2-pyrone natural products nectriapyrone, aplysiopsenes A-C, ent-aplysiopsene D, phomapyrones A and D, and of 8,9-dehydroxylarone were achieved by Wittig olefination starting with vermopyrone. Infectopyrone was synthesized by Horner-Wadsworth-Emmons reaction starting with phomapyrone D. Racemic phomapyrone C methyl ether was obtained by hydrogenation of nectriapyrone. The total syntheses were achieved starting from commercially available 3,5-heptanedione and led to the desired natural products in 18-46% over 5-6 steps, whereupon all five-step syntheses were carried out with a single chromatographic workup. The total synthesis of infectopyrone, aplysiopsenes A-D, of phomapyrones A and D, and of 8,9-dehydroxylarone were achieved for the first time, giving unambiguous proof for the proposed structures of these natural products. (C) 2012 Elsevier Ltd. All rights reserved.
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