Studies aimed at the total synthesis of the antitumor antibiotic cochleamycin A. An enantioselective biosynthesis-based pathway to the AB bicyclic core

被引：34

作者：

Chang, JY ^{[1
]}

Paquette, LA ^{[1
]}

机构：

[1] Ohio State Univ, Evans Chem Labs, Columbus, OH 43210 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 02期

关键词：

D O I：

10.1021/ol0102592

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS A convergent, highly enantioselective synthesis of the fully functionalized AB sector of cochleamycin A is described. A pair of building blocks, crafted from L-malic and L-ascorbic acids, are conjoined in a manner that gives rise to an (E,Z,E)-1,6,8-nonatriene. On heating, the latter undergoes stereocontrolled intramolecular Diels-Alder cyclization via an endo transition state.

引用

页码：253 / 256

页数：4

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