A ROUTE TO SEVERAL STEREOISOMERS OF CASTANOSPERMINE

被引:46
作者
BURGESS, K [1 ]
CHAPLIN, DA [1 ]
HENDERSON, I [1 ]
PAN, YT [1 ]
ELBEIN, AD [1 ]
机构
[1] UNIV ARKANSAS MED SCI HOSP,DEPT BIOCHEM & MOLEC BIOL,LITTLE ROCK,AR 72205
关键词
D O I
10.1021/jo00030a014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The following three stereoisomers of castanospermine have been prepared: (1R,6R,7R,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (1), (1R,6S,7S,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (2), and (1R,6R,7S,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (3). Each of these compounds was synthesized via asymmetric allylation of pentose derivatives with [(Z)-gamma-(methoxymethoxy)allyl]diisopinocampheylborane, an approach which is, in principle, suitable for preparations of a total of eight stereoisomers of castanospermine. Compounds 1-3 were tested as possible inhibitors of various glycosidase enzymes and for anti-HIV-1 activity in cell cultures. They are very poor inhibitors of glycosidase enzymes; however, preliminary tests indicate indolizidines 1 and 3 have weak but significant anti-HIV activities.
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页码:1103 / 1109
页数:7
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