RADICAL CYCLIZATIONS ON SUGAR TEMPLATES - STEREOSELECTIVE SYNTHESIS OF FUSED GAMMA-BUTYROLACTONES OF CARBOHYDRATES

被引：10

作者：

VELAZQUEZ, S ^{[1
]}

CAMARASA, MJ ^{[1
]}

机构：

[1] CSIC,INST QUIM MED,E-28006 MADRID,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(00)86290-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A stereoselective method is described for the synthesis of [3.3.0] fused lactones (gamma-butyrolactones) of carbohydrates at the 2 and 3 positions of the furanose ring, by intramolecular addition of radicals onto the alpha-position of alpha,beta-unsaturated esters. A new stereogenic center is formed at an off-template site of the ribofuranose ring, with good diastereoselectivity. Stereocontrol is discussed on the basis of conformational preference in the transition state. These gamma-butyrolactones of carbohydrates are useful chiral synthons for the preparation of branched-chain sugars. Opening of the lactone ring afforded homochiral branched-chain sugars having a highly functionalized C-branch at C-2 or C-3.

引用

页码：2141 / 2154

页数：14

共 36 条

[1] SYNTHESIS OF HOMOCHIRAL TRISUBSTITUTED GAMMA-BUTYROLACTONES [J].