Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines.

被引：11

作者：

Simoni, D

Roberti, M

Rondanin, R

Kozikowski, AP

机构：

[1] Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy

[2] Univ Bologna, Dipartimento Sci Farmaceut, I-40126 Bologna, Italy

[3] Georgetown Univ, Med Ctr, Drug Discovery Program, Inst Cognit & Computat Sci, Washington, DC 20007 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(99)00763-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective deprotonation of the 8-oxabicyclo[3.2.l]octan-3-one with chiral lithium amides 5 and 6, in the presence of LiCl, gave the chiral lithium enolates which were in turn reacted with methyl cyanoformate. The resulting chiral beta-keto esters were reduced with sodium amalgam to afford the 8-oxa-ecgonine- and 8-oxa-pseudoecgonine-like derivatives which allowed facile preparation of the (+)- and (-)-8-oxa-norcocaines and (+)- and (-)-8-oxa-pseudonorcocaines. The new synthesized 8-oxa analogues of cocaine showed good enantiomeric excesses in the range of 84-90%. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4425 / 4428

页数：4

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