Rigid dipeptide mimetics. stereocontrolled synthesis of all eight stereoisomers of 2-oxo-3-(N-Cbz-amino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid ester

被引：48
作者：
Mulzer, J
Schülzchen, F
Bats, JW
机构：
[1] Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria
[2] Free Univ Berlin, Inst Organ Chem, D-14195 Berlin, Germany
[3] Univ Frankfurt, Inst Organ Chem, D-60439 Frankfurt, Germany
来源：
TETRAHEDRON | 2000年 / 56卷 / 25期
关键词：
amino acids; peptide mimetics; stereoselection; allylation;
D O I：
10.1016/S0040-4020(00)00355-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereopure 2-oxo-3-(N-Cbz-amino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid (AZABIC) methyl and ethyl esters (14a/b and 23a/b, respectively) have been synthesized from readily available (R)- and (S)-pyroglutamic esters 1 and 15. Altogether all eight possible stereoisomers of this type of compound have been prepared in gram quantities. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4289 / 4298
页数：10
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