Asymmetric total synthesis of (-)-panacene and correction of its relative configuration

被引：59

作者：

Boukouvalas, John ^{[1
]}

Pouliot, Martin

Robichaud, Joel

MacNeil, Stephen

Snieckus, Victor

机构：

[1] Univ Laval, Dept Chim, Quebec City, PQ G1K 7P4, Canada

[2] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 16期

关键词：

D O I：

10.1021/ol061385e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of (-)-panacene has been accomplished in concise, highly stereoselective fashion from commercially available 2-methoxy6-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.

引用

页码：3597 / 3599

页数：3

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