（-）-5,11-去氧河豚毒素的改进合成。

An improved synthesis of (-)-5,11-dideoxytetrodotoxin.

机构信息

Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.

出版信息

J Org Chem. 2013 Feb 15;78(4):1699-705. doi: 10.1021/jo302773f. Epub 2013 Jan 30.

DOI:10.1021/jo302773f

PMID:23323757

Abstract

We describe an improved synthesis of (-)-5,11-dideoxytetrodotoxin from an enone, which was used for synthesis of tetrodotoxin and its analogues in this laboratory. One of the major modifications was to establish a two-step guanidinylation of trichloroacetamide of a highly functionalized intermediate, which allowed us to prepare (15)N(2)-labeled 5,11-dideoxytetrodotoxin for biosynthetic investigations.

摘要

我们描述了从烯酮改进合成 (-)-5,11-二脱氧河豚毒素的方法，该烯酮曾被用于本实验室中河豚毒素及其类似物的合成。主要的改进之一是建立了高度功能化中间体三氯乙酰胺的两步胍基化反应，这使我们能够为生物合成研究制备 (15)N(2)-标记的 5,11-二脱氧河豚毒素。