Asymmetric synthesis of 1,3-dithiolane nucleoside analogues

被引：6

作者：

Caputo, R

Guaragna, A

Palumbo, G

Pedatella, S

机构：

[1] Univ Naples Federico II, Dipartimento Chim Organ & Biochim, I-80126 Naples, Italy

[2] Consorzio Interuniv Nazl, I-30175 Marghera, VE, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 02期

关键词：

nucleosides; sulfur heterocycles; chirality; sulfoxides; antiviral agents;

D O I：

10.1002/ejoc.200390040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the ready asymmetric synthesis of nucleoside analogues containing a 1,3-dithiolane ring that mimics the sugar moiety of natural nucleosides. The synthesis is accomplished in three main steps from benzoyloxyethanal 1,3-dithiolane, the key step being its conversion into a chiral monosulfoxide by a modified Sharpless sulfo-oxygenation reaction. The nucleoside analogues were obtained in good overall yields and with excellent enantiomeric excesses. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

引用

页码：346 / 350

页数：5

共 21 条

[1] A NOVEL CLASS OF 1,3-OXATHIOLANE NUCLEOSIDE ANALOGS HAVING POTENT ANTI-HIV ACTIVITY [J].