SYNTHESIS OF PSEUDO-RIBOFURANOSES BY STEREOCONTROLLED REACTIONS ON 4-HYDROXYCYCLOPENT-2-ENYLMETHANOL DERIVATIVES

被引：18

作者：

SHOBERU, KA

ROBERTS, SM

机构：

[1] Department of Chemistry, University of Exeter, Exeter

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 18期

关键词：

D O I：

10.1039/p19920002419

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diol 3 is a major product formed from a Prins reaction on cyclopentadiene and was readily converted into the derivatives 4-7. The latter compounds were obtained in states of high optical purity by using both enzyme-catalysed hydrolysis and esterification reactions. Osmium tetraoxide transformed the ene diol derivatives 4-7 into the corresponding alcohols 8-11. In this way the alcohol (+)-6 was used to prepare (-)-pseudo-beta-ribofuranose (-)-2, and the alcohol (-)-4 was used to synthesize (+) -pseudo-alpha-ribofuranose (+)-1.

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页码：2419 / 2425

页数：7

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