ALLIUM CHEMISTRY - SIMPLE SYNTHESES OF ANTITHROMBOTIC CEPAENES FROM ONION AND DEOXYCEPAENES FROM OIL OF SHALLOT BY REACTION OF 1-PROPENETHIOLATE WITH SULFONYL HALIDES

被引:22
作者
BLOCK, E
ZHAO, SH
机构
[1] Department of Chemistry, State University of New York at Albany, Albany
关键词
D O I
10.1021/jo00048a007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoisomers of MeCH=CHSLi from Li/NH3 reduction of MeCH=CHSPr react with varying proportions of MsCl giving the respective stereoisomers of either bis(1-propenyl) disulfide (1), S-1-propenyl methane-sulfonothiate (2a), or 6-ethyl-4,5,7-trithiadeca-2,8-diene (3); oxidation of 3, a shallot oil component, gives 6-ethyl-4,5,7-trithiadeca-2,8-diene 7-oxide (cepaene, 4), an antithrombotic compound from onion.
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页码:5815 / 5817
页数:3
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