Diastereoselective IBX Oxidative Dearomatization of Phenols by Remote Induction: Towards the Epicocconone Core Framework

被引：24

作者：

Boulange, Agathe ^{[1
]}

Peixoto, Philippe A. ^{[1
]}

Franck, Xavier ^{[1
]}

机构：

[1] Univ Rouen, INSA Rouen, CNRS UMR 6014, COBRA IRCOF, F-76131 Mont St Aignan, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 37期

关键词：

diastereoselectivity; iodine; lactones; natural products; oxidative dearomatization; O-IODOXYBENZOIC ACID; IODINE(V) REAGENTS; BETA-CYCLODEXTRIN; HYPERVALENT; SIBX; SPIROLACTONIZATION; REACTIVITY; WATER;

D O I：

10.1002/chem.201101681

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The IBX twist does it: Towards the synthesis of a recently isolated dihydropyranic azaphilone core framework, a 2-iodoxybenzoic acid (IBX)-mediated oxidative dearomatization was performed on a bicyclic substrate with excellent diastereoselectivity. Trifluoroacetic acid (TFA) esters were obtained as single diastereomers and water was shown to increase both the speed and diastereoselectivity of the reaction (see scheme). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10241 / 10245

页数：5

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