Synthesis and conformational analysis of new cyclobutane-fused nucleosides

被引：33

作者：

Alibés, R ^{[1
]}

Alvárez-Larena, A ^{[1
]}

de March, P ^{[1
]}

Figueredo, M ^{[1
]}

Font, J ^{[1
]}

Parella, T ^{[1
]}

Rustullet, A ^{[1
]}

机构：

[1] Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Spain

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 03期

关键词：

D O I：

10.1021/ol052794y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A stereselective synthesis of 3-oxabicyclo[3.2.0]heptane nucleoside analogues, which were designed as conformational mimics of the anti-HIV agents 2',3'-didehydro-2',3'-dideoxythimidine (stavudine, d4T) and 2',3'-didehydro-2',3'-dideoxyadenosine (MA), is described. The target compounds were prepared by condensation of a common intermediate bicyclic acetate, derived from a homochiral 2(5H)-furanone, with pyrimidine and purine bases under modified Vorbruggen conditions. The conformational behavior of the synthesized nucleoside analogues was studied by NMR spectroscopy and X-ray crystallography.

引用

页码：491 / 494

页数：4

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