SYNTHESIS OF (PLUS-OR-MINUS)-2-BETA-HYDROXY-6-ALPHA-ACETOXYNORTROPANE

被引：6

作者：

PEI, XF

SHEN, JX

机构：

[1] Laboratory of Medicinal Chemistry, National Institutes of Pharmaceutical Research and Development, Beijing, 100083

来源：

HETEROCYCLES | 1993年 / 36卷 / 11期

关键词：

D O I：

10.3987/COM-93-6480

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

8-Benzyl-6alpha-chloro-6beta-carbonitrile-2,2-ethylgnedioxy-8-azabicyclo[3.2.1]oct-3-ene (8) and its C(6) epimer (9) were hydrolyzed to afford 6-ketone (10). Reduction of the ketone (10) with sodium borohydride gave predominantly 6alpha-ol (14). 2-Ketone (20), obtained from 14 by deprotection followed by hydrogenation and acetylation, was reduced with sodium borohydride to give 2beta-ol a as the major epimer. Nortropane (24) was prepared from 21 by debenzylation.

引用

页码：2549 / 2556

页数：8

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