Synthesis of Purine Nucleosides Built on a 3-Oxabicyclo[3.2.0]heptane Scaffold

被引：28
作者：
Flores, Ramon [1 ]
Rustullet, Albert [1 ]
Alibes, Ramon [1 ]
Alvarez-Larena, Angel [2 ]
de March, Pedro [1 ]
Figueredo, Marta [1 ]
Font, Josep [1 ]
机构：
[1] Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Spain
[2] Univ Autonoma Barcelona, Unitat Crystal Lografia, Bellaterra 08193, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 13期
关键词：
VIRUS TYPE-1 INFECTION; ANTI-HIV ACTIVITY; ANTIVIRAL ACTIVITY; DIASTEREOSELECTIVE SYNTHESIS; FLUORINATED NUCLEOSIDES; 2+2 PHOTOCYCLOADDITION; ACID; 2(5H)-FURANONES; CYCLOBUTANE; ADENINE;
D O I：
10.1021/jo200775x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The photochemical [2 + 2] cycloaddition of chiral 3-chloro and 3-fluoro-5-hydroxymethyl-2(5H)-furanone to ethylene and acetylene has been studied. The effect of the halogen atom on the chemical yield and facial diastereoselectivity of the cycloaddition process has been evaluated. From the major anti cycloadducts, practical syntheses of several purine cyclobutane and cyclobutene-fused nucleosides containing a halogen atom have been developed. The anti-HIV activity of the new nucleoside analogues has been evaluated.
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收藏
页码：5369 / 5383
页数：15
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