Skeletal rearrangements of bicyclo[2.2.2]lactones:: a short and efficient route towards Corey's lactone

被引：28

作者：

Augustyns, B ^{[1
]}

Maulide, N ^{[1
]}

Markó, IE ^{[1
]}

机构：

[1] Univ Catholique Louvain, Dept Chim, B-1348 Louvain, Belgium

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 22期

关键词：

lactones; bicyclic; radical; rearrangement; Corey's lactone; 3-CMP; Diels-Alder;

D O I：

10.1016/j.tetlet.2005.03.204

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The application of a unique tandem radical-initiated, Bronsted acid-catalysed, skeletal rearrangement of bicyclo[2.2.2]-lactones provides a novel route towards Corey ' s lactone 2. The strategy also features a high-pressure promoted inverse election-demand Diels-Alder (IEDDA) reaction of 3-carbomethoxy-2-pyrone (3-CMP), which proceeds with complete regio- and diastereocontrol. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3895 / 3899

页数：5

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