A CHIRAL SYNTHESIS OF (-)-CANNABISATIVINE - AN APPLICATION OF THE HIGHLY DIASTEREOSELECTIVE HETERO-DIELS-ALDER REACTION

被引：34

作者：

HAMADA, T

ZENKOH, T

SATO, H

YONEMITSU, O

机构：

[1] Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(00)74295-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The polyamine alkaloid cannabisativine was synthesized as an optical active form. The key step is the hetero Diels-Alder reaction of chiral diene and an N-tosylimine, in which regio- and diastereo-face selectivities were completely controlled, only one diastereomer was isolated in high yield. Synthesized (-)-cannabisativine has the same physical data as the natural product except for the alpha-D value.

引用

页码：1649 / 1652

页数：4

共 12 条

[1] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].