Chromium(0)-promoted multicomponent cycloaddition of tethered diynes with cyclic trienes:: Application to the total synthesis of 9-epi-pentalenic acid

被引：27

作者：

Rigby, JH ^{[1
]}

Laxmisha, MS ^{[1
]}

Hudson, AR ^{[1
]}

Heap, CH ^{[1
]}

Heeg, MJ ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 20期

关键词：

D O I：

10.1021/jo040204o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient protecting group controlled regioselective chromium(0)-mediated three-component higher order cycloaddition of tethered diynes with cyclic trienes that generates five rings and six stereogenic centers in one step is described. Following a sequence of reactions featuring a chemoselective Baeyer-Villiger rearrangement and a regioselective cyclopropane hydrogenolysis, the total synthesis of 9-epi-pentalenic acid was achieved.

引用

页码：6751 / 6760

页数：10

共 90 条

[1] HIGHLY STEREOCONTROLLED AND REGIOCONTROLLED CYCLOPENTANNULATION VIA ALLYLPHOSPHONATE CONJUGATE ADDITION AND HYDROBORATION OXIDATION ELIMINATION - SYNTHESIS OF PENTALENIC ACID WITH VIRTUALLY COMPLETE STEREOCONTROL AND REGIOCONTROL [J].