Total synthesis of (+)-aquaticol by biomimetic phenol dearomatization:: Double diastereofacial differentiation in the Diels-Alder dimerization of orthoquinols with a C2-symmetric transition state

被引：31

作者：

Gagnepain, Julien

Castet, Frederic

Quideau, Stephane

机构：

[1] Inst Europeen Chim & Biol, F-33607 Pessac, France

[2] Univ Bordeaux 1, Lab Chim Organ & Organomet, CNRS, UMR 5802, F-33405 Talence, France

[3] Univ Bordeaux 1, Lab Physicochim Mol, CNRS, UMR 5803, F-33405 Talence, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 09期

关键词：

cycloaddition; dearomatization; diastereoselectivity; hyperconjugation; hypervalent compounds;

D O I：

10.1002/anie.200604610

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Double or nothing: The bissesquiterpene (+)-aquaticol was synthesized by biomimetic oxidative dearomatization of 1 via an orthoquinol intermediate that undergoes spontaneous and selective dimerization; only like diastereomers react. The remarkable double diastereofacial differentiation observed is explained in terms of a double hyperconjugative Cieplak-Fallis" effect expressed in a C 2-symmetric bispericyclic transition state. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA."

引用

页码：1533 / 1535

页数：3

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