Stereo-random synthesis of highly functionalized proline analogues by azomethine cycloaddition

被引：11

作者：

Henkel, B ^{[1
]}

Stenzel, W ^{[1
]}

Schotten, T ^{[1
]}

机构：

[1] Lilly Forsch GmbH, D-22419 Hamburg, Germany

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2000年 / 10卷 / 09期

关键词：

D O I：

10.1016/S0960-894X(00)00143-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 [药物化学];

摘要：

Highly substituted proline analogues were synthesized on Wang-resin bearing bisprotected histidine as starting material. The proline analogues (1,5-diazabicyclo[3.3.0]octane-2-carboxylic acid) were generated by 1,3-dipolar cycloaddition of azomethine ylides with maleimides, thus creating a library of maximum stereochemical diversity. Every compound set with the same empirical formula can theoretically consist of four diastereomers and can be tested in biological assays as mixture. Additionally different methods for the acylation of the proline nitrogen were evaluated. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：975 / 977

页数：3

共 14 条

[1]

[Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3

[2]

X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .15. AMINE GENERATED AZAALLYL ANIONS VERSUS METALLO-1,3-DIPOLES IN CYCLO-ADDITIONS OF ALPHA-AMINO-ACID ESTERS - FACILE REGIO-SPECIFIC AND STEREO-SPECIFIC FORMATION OF PYRROLIDINES [J].