A stereoselective carbohydrate route to optically active furo[2,3-b]benzofuran ring system

被引：2
|
作者：
Lakshmi, R [1 ]
Balasubramanian, KK [1 ]
机构：
[1] Shasun Chem & Drugs Ltd, Madras 600036, Tamil Nadu, India
来源：
ARKIVOC | 2003年
关键词：
aflatoxin; furo[2,3-b]benzofuran; stereoselective synthesis; tri-O-acetyl-D-glucal; Ferrier rearrangement; Claisen rearrangement;
D O I：
10.3998/ark.5550190.0004.314
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A stereoselective synthesis of the furo[2,3-b] benzofuran ring system 8, commonly encountered in aflatoxins has been achieved by exploiting the inherent chirality of D-glucose. Ozonolysis of 4, followed by selective hydrolysis of the formate ester intermediate 6, yielded directly the target ring system 8, in good over all yields leading to the right stereochemistry at the ring junction corresponding to the naturally occurring isomer of aflatoxin.
引用
收藏
页码：140 / 145
页数：6
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