Diastereoselective synthesis of homo-N,O-nucleosides

被引：34

作者：

Chiacchio, U

Genovese, F

Iannazzo, D

Librando, V

Merino, P

Rescifina, A

Romeo, R

Procopio, A

Romeo, G

机构：

[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy

[2] Univ Messina, Dipartimento Farmacochim, I-98168 Messina, Italy

[3] Univ Zaragoza, CSIC, Fac Ciencias, ICMA,Dept Quim Organ, E-50009 Zaragoza, Aragon, Spain

来源：

TETRAHEDRON | 2004年 / 60卷 / 02期

关键词：

N-methyl-C-ethoxycarbonyl nitrone; C-alpha-silyloxymethyl-N-methyl nitrone; nucleobases;

D O I：

10.1016/j.tet.2003.11.007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new class of homo-N,O-nucleosides has been designed, based on the 1,3-dipolar cycloaddition of C-substituted nitrones with allyl nucleobases. The N-methyl-C-ethoxycarbonyl nitrone 1, and the C-alpha-silyloxymethyl-N-methyl nitrone 7 have been exploited: the stereochemical features of the obtained nucleosides are dependent on the nature of the dipole. The results obtained with DFT calculations fully agree with the experimental results and successfully reproduce the experimentally observed reversal of endo/exo selectivity for nitrones I and 7. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：441 / 448

页数：8

共 28 条

[1] Heterocyclic nucleoside analogues by cycloaddition reactions of 1-vinylthymine with 1,3-dipoles [J].