Synthesis of the Leu-Trp Component of the Celogentin Family of Cyclic Peptides Through a C-H Activation-Cross-Coupling Strategy

被引：27

作者：

Li, Barbara T. Y. ^{[1
,2
]}

White, Jonathan M. ^{[1
,2
]}

Hutton, Craig A. ^{[1
,2
]}

机构：

[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia

[2] Univ Melbourne, Mol Sci & Biotechnol Inst Bio21, Melbourne, Vic 3010, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2010年 / 63卷 / 03期

基金：

澳大利亚研究理事会;

关键词：

ANTIMITOTIC BICYCLIC PEPTIDES; ACID METHYL-ESTER; CELOSIA-ARGENTEA; STEPHANOTIC ACID; LAPORTEA-MOROIDES; SEEDS; COMPLESTATIN; RESIDUE;

D O I：

10.1071/CH10033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A bioinspired approach to the central leucine(C3)-tryptophan(C6) cross-linked moiety present in the celogentin family of cyclic peptide natural products was achieved. The key transformation was enabled through a palladium-catalyzed C-H activation-cross-coupling of leucine quinoline amide and 6-iodotryptophan derivatives. X-Ray crystallographic analysis of a beta-(indol-6-yl)-leucine derivative confirms the stereochemistry of the cross-linked adduct matches that of the natural products. The method enables the preparation of the Leu-Trp adduct as a single stereoisomer from L-leucine and L-tryptophan.

引用

收藏

页码：438 / 444

页数：7

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