Metal-Catalyzed Derivatization of Cα-Tetrasubstituted Amino Acids and Their Use in the Synthesis of Cyclic Peptides

被引：17

作者：

Grauer, Andreas ^{[1
]}

Spaeth, Andreas ^{[1
]}

Ma, Dawei ^{[2
]}

Koenig, Burkhard ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany

[2] Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2009年 / 4卷 / 07期

关键词：

amino acids; cyclization; homogeneous catalysis; peptides; peptidomimetics; O BOND FORMATION; N-ARYLATION; BIOACTIVE PEPTIDES; CONTAINING HETEROCYCLES; COUPLING REACTIONS; HIV-1; PROTEASE; ARYL; TRIPEPTIDE; INHIBITORS; DESIGN;

D O I：

10.1002/asia.200900033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

C-alpha-tetrasubstituted amino acids are important building blocks in the design and preparation of novel peptidomimetics. We report on the functionalization of the C-alpha-tetrasubstituted THF amino acid rac-5 by copper(I) catalyzed N-arylation reactions. The aryl bromide substituent of rac-5 is replaced by a variety of aliphatic and aromatic amines. Intramolecular N-arylation yielded only small amounts of a cyclic tripeptide 2, whereas cyclic tripeptide ethers 4 and 50 were obtained in an enantiomerically pure form from a palladium(0)-catalyzed intramolecular O-arylation.

引用

页码：1134 / 1140

页数：7

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