Total synthesis of infectopyrone, aplysiopsenes A-C, ent-aplysiopsene D, phomapyrones A and D, 8,9-dehydroxylarone, and nectriapyrone

被引：26

作者：

Geiseler, Oliver ^{[1
]}

Podlech, Joachim ^{[1
]}

机构：

[1] KIT, Inst Organ Chem, D-76131 Karlsruhe, Germany

来源：

TETRAHEDRON | 2012年 / 68卷 / 36期

关键词：

Polyketides; Fungal metabolites; Olefination; 2-Pyrones; Total synthesis; ALPHA-PYRONES; BIOSYNTHESIS; FUNGI;

D O I：

10.1016/j.tet.2012.06.104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：7280 / 7287

页数：8

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