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
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
收藏
页码:1649 / 1652
页数:4
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