Synthesis of the chlorofusin cyclic peptide: Assignment of the asparagine stereochemistry

被引：22

作者：

Desai, P

Pfeiffer, SS

Boger, DL

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 26期

关键词：

D O I：

10.1021/ol036083g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An efficient synthesis of two diastereomers of the chlorofusin cyclic peptide bearing either the L-Asn3/D-Asn4 or D-Asn3/L-Asn4 stereochemistry is detailed. Four key subunits were prepared, sequentially coupled, and cyclized to provide the two diastereomeric macrocycles. The absolute stereochemistry at the asparagine residues 3 and 4 was assigned as L and D, respectively, by correlating the NMR data of the two diastereomers with that reported for the natural product.

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页码：5047 / 5050

页数：4

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