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通过三条路线从肌醇和 D-葡萄糖立体控制全合成河豚毒素:构建具有支链结构的复杂多官能化环糖醇的方法

Stereocontrolled total synthesis of tetrodotoxin from myo-inositol and D-glucose by three routes: aspects for constructing complex multi-functionalized cyclitols with branched-chain structures.

作者信息

Sato Ken-ichi, Akai Shoji, Yoshimura Juji

机构信息

Department of Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan.

出版信息

Nat Prod Commun. 2013 Jul;8(7):987-98.

PMID:23980434
Abstract

This report describes the stereocontrolled total synthesis of the multi-functionalized cyclitol derivative, tetrodotoxin, containing eight asymmetric carbons and different types of branched-chains, from myo-inositol and D-glucose using three different methods. The tetrodotoxin derivatives possess a relatively small molecular weight but unique structural and chemical properties. Selection of the appropriate synthetic method may be useful not only for compounds related to TTX (including related derivatives), but also for other highly complex multi-functionalized cyclitols containing branched-chains.

摘要

本报告描述了使用三种不同方法,从肌醇和D -葡萄糖出发,立体控制全合成多功能环糖醇衍生物河豚毒素的过程。河豚毒素含有八个不对称碳原子和不同类型的支链。河豚毒素衍生物分子量相对较小,但具有独特的结构和化学性质。选择合适的合成方法不仅对与TTX相关的化合物(包括相关衍生物)有用,而且对其他含有支链的高度复杂的多功能环糖醇也有用。

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