SYNTHESIS OF A 16-MEMBERED CYCLIC PEPTIDE MODEL OF THE BCF RINGS OF RISTOCETIN-A USING ARENE-RUTHENIUM CHEMISTRY COUPLED WITH CYCLOAMIDATION

被引：38

作者：

PEARSON, AJ

LEE, K

机构：

[1] Department of Chemistry, Case Western Reserve University, Cleveland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 22期

关键词：

D O I：

10.1021/jo00127a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent synthetic approach to the cyclic peptide 4, which is a model for the B/C/F ring system of ristocetin B, is described. A key reaction is the coupling of the phenolic dipeptide 5, constructed from arylglycine subunits, with the chlorophenylalanine-RuCp cationic complex 6, followed by demetalation of the product to give the diaryl ether 7, without epimerization at any of the amino acid residues. Deprotection of 7 followed by cycloamidation affords the target molecule 4, produced as a mixture of atropdiastereomers which were separated and characterized by NMR spectroscopy.

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页码：7153 / 7160

页数：8

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