An Improved Synthesis of (-)-5,11-Dideoxytetrodotoxin

被引：25

作者：

Adachi, Masaatsu ^{[1
]}

Imazu, Takuya ^{[1
]}

Isobe, Minoru ^{[1
]}

Nishikawa, Toshio ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Bioagr Sci, Organ Chem Lab, Chikusa Ku, Nagoya, Aichi 4648601, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 04期

基金：

日本学术振兴会;

关键词：

EFFICIENT TOTAL-SYNTHESIS; OPTICALLY-ACTIVE TETRODOTOXIN; ASYMMETRIC TOTAL-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; UNNATURAL ANALOG; 8,11-DIDEOXYTETRODOTOXIN; (-)-TETRODOTOXIN; ROUTE;

D O I：

10.1021/jo302773f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 N-15(2)-labeled 5,11-dideoxytetrodotoxin for biosynthetic investigations.

引用

页码：1699 / 1705

页数：7

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