Generation of homochiral aziridinium ion intermediates derived from 2,3-epoxy amines: Regiospecific nucleophilic trapping with nitrogen nucleophiles. Application in the synthesis of novel morpholinosphingolipid analogues with potential glucosylceramide synthase inhibitory activity

被引:29
作者
Liu, QY
Marchington, AP
Boden, N
Rayner, CM
机构
[1] UNIV LEEDS, SCH CHEM, LEEDS LS2 9JT, W YORKSHIRE, ENGLAND
[2] UNIV LEEDS, CTR SELF ORG MOL SYST, LEEDS LS2 9JT, W YORKSHIRE, ENGLAND
[3] PFIZER LTD, CENT RES, DEPT DISCOVERY CHEM, SANDWICH CT13 9NJ, KENT, ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 04期
关键词
D O I
10.1039/a604534k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Lewis acid induced rearrangement of 2,3-epoxy amines into the corresponding 2-trimethylsilyloxymethylaziridinium ions is described, Such intermediates have been characterised by H-1 NMR spectroscopy, and react with nitrogen nucleophiles regiospecifically to form 1-substituted 2,3-amino alcohols in good to excellent yields and with full stereochemical control, This methodology has been applied to the synthesis of a potential inhibitor of glucosylceramide synthase, a promising target for cancer chemotherapy.
引用
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页码:511 / 525
页数:15
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