1-HYDROXY-3-AMINO-2-PIPERIDONE (DELTA-N-HYDROXYCYCLOORNITHINE) DERIVATIVES - KEY INTERMEDIATES FOR THE SYNTHESIS OF HYDROXAMATE-BASED SIDEROPHORES

被引：46

作者：

KOLASA, T ^{[1
]}

MILLER, MJ ^{[1
]}

机构：

[1] UNIV NOTRE DAME,DEPT CHEM,NOTRE DAME,IN 46556

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 06期

关键词：

D O I：

10.1021/jo00293a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several routes for the synthesis of -N-(benzyloxy)cycloornithine (2) from glutamic acid derived starting materials are described. Efficient methods were developed for the synthesis of glutamic acid 7-semialdehyde and 5-hydroxynorvaline derivatives as key substrates for preparation of N-hydroxyornithine analogues. Thus, the best approaches to the synthesis of 2 were: (1) reductive cyclization of an N-hydroxysuccinimide ester of the O-benzyloxime 4 of a-amino-protected glutamic acid 7-semialdehyde 5 and (2) cyclization of the N- (benzyloxy)amide of 6-bromonorvaline (7). © 1990, American Chemical Society. All rights reserved.

引用

页码：1711 / 1721

页数：11

共 40 条

[31] THE PREPARATION OF N-PROTECTED AMINO-ALCOHOLS AND N-PROTECTED PEPTIDE ALCOHOL BY REDUCTION OF THE CORRESPONDING ESTERS WITH SODIUM-BOROHYDRIDE - AN IMPROVED PROCEDURE INVOLVING A SLOW ADDITION OF A SMALL AMOUNT OF METHANOL [J].