用于合成C-芳基吡喃糖苷的立体选择性方法，该方法解决了睑萼毒素E中C7取代的问题。

Stereoselective approach to C-aryl pyranoside synthesis which addresses the problem of C7-substitution in blepharocalyxin E.

作者信息

Cakir Sidika Polat, Mead Keith T

机构信息

Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA.

出版信息

J Org Chem. 2004 Mar 19;69(6):2203-5. doi: 10.1021/jo0355909.

DOI:10.1021/jo0355909

PMID:15058975

Abstract

A general route to a series of aryl-substituted pyranoside derivatives has been developed as a model for the synthesis of blepharocalyxin E. Two exo-substituted tetrahydro-4H-furo[2,3-b]pyran-2-one derivatives, 8a and 8b, were prepared and treated separately with anisole and phenoxytriisopropylsilane under Lewis acid conditions to effect C-aryl pyranoside synthesis. In each case, a gamma-lactone was formed, which rearranged to the desired structure on acid treatment. Four compounds (12, 14, 16, and 18) were prepared by this route as single isomers in good overall yield.

摘要

已开发出一条合成一系列芳基取代吡喃糖苷衍生物的通用路线，作为合成睑萼毒素E的模型。制备了两种外取代的四氢-4H-呋喃并[2,3-b]吡喃-2-酮衍生物8a和8b，并在路易斯酸条件下分别用苯甲醚和苯氧基三异丙基硅烷处理，以实现C-芳基吡喃糖苷的合成。在每种情况下，都会形成γ-内酯，经酸处理后重排为所需结构。通过该路线制备了四种化合物（12、14、16和18），均为单一异构体，总收率良好。