Practical stereoselective synthesis of conformationally constrained unnatural proline-based amino acids and peptidomimetics

被引：45

作者：

Belvisi, L

Colombo, L

Colombo, M

Di Giacomo, M

Manzoni, L

Vodopivec, B

Scolastico, C

机构：

[1] Univ Pavia, Dipartimento Chim Farmaceut, I-27100 Pavia, Italy

[2] Univ Milan, Dipartimento Chim Organ & Ind, Ctr CNR, I-20133 Milan, Italy

[3] Univ Milano Bicocca, Dipartimento Biotecnol & Biosci, I-20126 Milan, Italy

来源：

TETRAHEDRON | 2001年 / 57卷 / 30期

关键词：

ring-closing metathesis; unnatural amino acids; octahydroindole ring; peptidomimetics;

D O I：

10.1016/S0040-4020(01)00538-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical synthetic scheme was developed to prepare both the cis- and trans-fused stereoisomers of N-Boc-L-octahydroindole-2-carboxylic acid (L-Oic) methyl ester. Key event of the synthetic sequence was the ring-closing metathesis of a suitable diallylated proline derivative. This is the first reported practical synthesis of the trans-fused isomer. Functionalization of the octahydroindole nucleus by electrochemical oxidation followed by acid-catalysed allylation paved the way for the preparation of reverse-turn dipeptide mimics. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6463 / 6473

页数：11

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