AMINO-ACIDS .12. (+/-)PIPECOLIC ACID-DERIVATIVES .2. AN EXPEDIENT SYNTHETIC ENTRY TO SUBSTITUTED PIPECOLIC ACIDS

被引：13

作者：

HERDEIS, C

ENGEL, W

机构：

[1] Institut für Pharmazie und Lebensmittelchemie, Universität Würzburg, Würzburg, D-8700, Am Hubland

来源：

ARCHIV DER PHARMAZIE | 1992年 / 325卷 / 07期

关键词：

D O I：

10.1002/ardp.19923250709

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The Diels-Alder product 1 is transformed by Noyori reaction and catalytic hydrogenation to 4. Hydrolysis with concomitant decarboxylation of 4 furnishes the trans configuration amino acid 5. Functional group transformation (reduction, lactonization) of 5 provides 7, ring opening affords the pipecolic acid derivative 9. On the other hand 1 is hydrolyzed to 10 and 4-oxo-pipecolic acid 11. Reduction of 10 and subsequent hydrolysis with decarboxylation of 12 affords the amino acid 13a/13b in a cis/trans ratio of 1:1. Contrary to this result, reduction of 11 provides 13a/13b in a ratio of greater-than-or-equal-to 95/5

引用

页码：419 / 423

页数：5

共 16 条

[1] STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED PIPECOLIC ACIDS [J].