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
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.
引用
收藏
页码:5047 / 5050
页数:4
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