Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes:: Incorporation of polyhydroxylated carbocyclic β-amino acids into peptides

被引：34
|
作者：
Soengas, RG [1 ]
Estévez, JC [1 ]
Estévez, RJ [1 ]
机构：
[1] Univ Santiago, Dept Quim Organ, Santiago De Compostela 15782, Spain
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 09期
关键词：
D O I：
10.1021/ol034127f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
graphic A promising new strategy for the transformation of nitrohexofuranoses into cyclopentylamines, based on intramolecular cyclization followed by controlled opening of the resulting 2-oxabicyclo[2.2.1]heptane derivatives, allowed the first total synthesis of a carbocyclic beta-amino acid and its incorporation into peptides. This strategy also afforded a new route to cyclopentylamines with well-known glycosidase inhibition properties.
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收藏
页码：1423 / 1425
页数：3
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