8,11-二脱氧河豚毒素（河豚毒素的非天然类似物）的立体控制合成。

Stereocontrolled synthesis of 8,11-dideoxytetrodotoxin, unnatural analogue of puffer fish toxin.

作者信息

Nishikawa Toshio, Urabe Daisuke, Yoshida Kazumasa, Iwabuchi Tomoko, Asai Masanori, Isobe Minoru

机构信息

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

出版信息

Org Lett. 2002 Aug 8;4(16):2679-82. doi: 10.1021/ol026177a.

DOI:10.1021/ol026177a

PMID:12153208

Abstract

[structure: see text] 8,11-Dideoxytetrodotoxin, an unnatural tetrodotoxin analogue, was synthesized in a highly stereoselective manner from a common intermediate in our synthetic studies on tetrodotoxin. The synthesis features neighboring group participation of trichloroacetamide for stereoselective hydroxylation, protection of ortho ester, and guanidine installation with Boc-protected isothiourea.

摘要

[结构：见正文] 8,11-二脱氧河豚毒素，一种非天然的河豚毒素类似物，在我们对河豚毒素的合成研究中，以高度立体选择性的方式从一个共同中间体合成。该合成的特点包括三氯乙酰胺的邻基参与以进行立体选择性羟基化、原酸酯的保护以及用Boc保护的异硫脲安装胍基。