New reactions and step economy:: the total synthesis of (±)-salsolene oxide based on the type II transition metal-catalyzed intramolecular [4+4] cycloaddition

被引：186

作者：

Wender, Paul A. ^{[1
]}

Croatt, Mitchell P.

Witulski, Bernhard

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

[2] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55099 Mainz, Germany

来源：

TETRAHEDRON | 2006年 / 62卷 / 32期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/j.tet.2006.02.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Studies on the viability of the type 11 nickel-catalyzed intramolecular [4+4] cycloaddition of bis-dienes show that it is influenced by both diene substitution and geometry. Both E- and Z-isomers of 19 and 20 react. albeit at markedly different rates. to afford cycloadducts. whereas only the Z-isomer of 9 (and not the E-isomer) reacts to give 8 and 25. Chemoselective elaboration of 8 to (+/-)-salsolene oxide (7) was used to confirm the cycloadduct structure while establishing a step economical route to the natural product. (c) 2006 Elsevier Ltd. All right reserved.

引用

页码：7505 / 7511

页数：7

共 41 条

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