两种哈根氏腺内酯的简短实用合成法。

A short and practical synthesis of two Hagen's gland lactones.

作者信息

Paz-Morales Evelyn, Melendres Ruth, Sartillo-Piscil Fernando

机构信息

Centro de Investigación de la Facultad de Ciencias Químicas, BUAP. 14 Sur Esq. San Claudio, San Manuel, Puebla, Mexico.

出版信息

Carbohydr Res. 2009 Jun 12;344(9):1123-6. doi: 10.1016/j.carres.2009.03.025. Epub 2009 Mar 26.

DOI:10.1016/j.carres.2009.03.025

PMID:19362711

Abstract

A seven-step total synthesis of Hagen's gland lactones 1 and 2 starting from 1,2-O-isopropylidene-alpha-D-xylofuranose 3 is reported. The success of this short and practical synthesis depends on the use of two key reactions: a stereoselective nucleophilic substitution at the anomeric position of 5 and 6, which allowed the construction of the gamma-lactone ring, and an alkyl substitution reaction on tosylated compound 4, which permitted the carbon chain elongation of the tetrahydrofuran ring appendage at C-6.

摘要

报道了从1,2-O-异丙叉基-α-D-木呋喃糖3出发，七步全合成哈根氏腺内酯1和2的方法。这种简短而实用的合成方法的成功取决于两个关键反应的使用：在5和6的异头位置进行立体选择性亲核取代，从而构建γ-内酯环；以及对甲苯磺酸酯化合物4进行烷基取代反应，从而使C-6位的四氢呋喃环附属物的碳链延长。