Enantioselective synthesis of homocarbocyclic-2′-oxo-3′-azanucleosides

被引:31
作者
Chiacchio, U
Saita, MG
Crispino, L
Gumina, G
Mangiafico, S
Pistarà, V
Romeo, G
Piperno, A
De Clercq, E
机构
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[2] Med Univ S Carolina, Dept Pharmaceut Sci, Charleston, SC 29425 USA
[3] Univ Messina, Dipartimento Farm Chim, I-98168 Messina, Italy
[4] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium
关键词
nucleosides; 1,3-dipolar cycloaddition; N-glycosyl nitrones;
D O I
10.1016/j.tet.2005.10.075
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective synthesis of homocarbocyclic-2'oxo-3'-azanucleosides has been performed by cycloaddition reaction of the N-glycosyl nitrones with allyl nucleobases. The use of nitrones originated from two different carbohydrates, the N-ribosyl nitrone and the N-mannosyl nitrone, proceeded in a stereocontrolled and predictable manner with a good degree of enantioselectivity, so allowing an easy entry to both enantiomers. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1171 / 1181
页数:11
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