Enantioselective total synthesis of the osteoclastogenesis inhibitor (+)-symbioimine

被引：20

作者：

Kim, Justin

Thomson, Regan J.

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

[2] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 17期

关键词：

biomimetic synthesis; cycloaddition; Diels-Alder reaction; natural products; total synthesis;

D O I：

10.1002/anie.200605160

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) No bones about it: The first enantioselective total synthesis of the osteoclastogenesis inhibitor (+)-symbioimine (1) has been achieved. The synthesis features a convergent enol silane addition to a dimethyl acetal and a key, possibly biomimetic, intramolecular Diels-Alder reaction promoted by a dihydropyridinium ion to build four of the five requisite stereocenters in one step. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

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页码：3104 / 3106

页数：3

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