Isoxazoline-carbocyclic aminols for nucleoside synthesis through aza-Diels-Alder reactions

被引：24
|
作者：
Quadrelli, Paolo
Piccanello, Andrea
Martinez, Naiara Vazquez
Bovio, Bruna
Mella, Mariella
Caramella, Pierluigi
机构：
[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
[2] Univ Pavia, Dipartimento Chim Gen, I-27100 Pavia, Italy
来源：
TETRAHEDRON | 2006年 / 62卷 / 31期
关键词：
D O I：
10.1016/j.tet.2006.05.029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel approach to useful aminols for the synthesis of carbocyclic nucleosides is reported starting from a convenient source, the 2-azanorborn-5-enes. These are readily available through the Grieco cycloaddition of cyclopentadiene with iminium salts and are reactive dipolarophiles toward nitrile oxides. The prolific elaboration of the isoxazoline cycloadducts allowed preparation of the target aminols through the unmasking of the hydroxymethylene group at the C3 level of the azanorbornene structure. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7370 / 7379
页数：10
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