Carbohydrates to densely functionalized carbocycles: 'Armed and disarmed' effects in an approach to tetrodotoxin

被引：33

作者：

Fraser-Reid, B ^{[1
]}

Burgey, CS

Vollerthun, R

机构：

[1] Duke Univ, Durham, NC 27706 USA

[2] Nat Prod & Glycotechnol Res Inst, NPG, Res Triangle Pk, NC USA

来源：

PURE AND APPLIED CHEMISTRY | 1998年 / 70卷 / 02期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1351/pac199870020285

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A sugar-based approach to tetrodotoxin begins with 1,6-anhydro-beta-D-mannopyranose, and exploits the differences between the sugar's various oxygens to effect regio-, chemo-, and stereoselective transformations in achieving an appropriately functionalized advanced intermediate of the target molecule. Free radical reactions are used in key situations, and also the propensity of caged intermediates to undergo adamantyl rearrangement/expansion is incorporated into the synthetic design.

引用

页码：285 / 288

页数：4

共 28 条

[1] CARBOHYDRATES TO CARBOCYCLES - SYNTHESIS OF THE DENSELY FUNCTIONALIZED CARBOCYCLIC CORE OF TETRODOTOXIN BY RADICAL CYCLIZATION OF AN ANHYDRO SUGAR PRECURSOR [J].