ENANTIOENRICHED N-(2-CHLOROALKYL)-3-ACETOXYPIPERIDINES AS POTENTIAL CHOLINOTOXIC AGENTS - SYNTHESIS AND PRELIMINARY EVIDENCE FOR SPIROCYCLIC AZIRIDINIUM FORMATION

被引:24
作者
HUH, N [1 ]
THOMPSON, CM [1 ]
机构
[1] LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
关键词
D O I
10.1016/0040-4020(95)00285-G
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses of six enantioenriched analogs representing cyclic forms of acetylcholine are reported. (S)- and (R)-N-(2-chloroethyl)-3-acetoxypiperidine and (R,R)-, (R,S)-, (S,R)-, and (S,S)-N-(2-chloropropyl)-3-acetoxypiperidine have been synthesized from (R)- or (S)-3-hydroxypiperidine in five steps. (R)- and (S)-3-hydroxypiperidine were accessed via parallel stereospecific routes from d- and 1-glutamic acid, and through fractional recrystallization of diastereomeric tartranilic acid salts. (S)-N-(2-Chloroethyl)-3-acetoxypiperidine was reacted with silver perchlorate to form a spirocyclic aziridinium analog of acetylcholine as evidenced by a characteristic H-1 NMR shift for the aziridinium methylene groups.
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页码:5935 / 5950
页数:16
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