ASPECTS OF THE CHEMISTRY OF DIOXOLANES - SYNTHESIS OF (C)UNDER-BAR-NUCLEOSIDE ANALOGS

Authors
MELLOR BJ MURRAY PE THOMAS EJ
Citation
Bj. Mellor et al., ASPECTS OF THE CHEMISTRY OF DIOXOLANES - SYNTHESIS OF (C)UNDER-BAR-NUCLEOSIDE ANALOGS, Tetrahedron, 54(1-2), 1998, pp. 243-256
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
1-2
Year of publication
1998
Pages
243 - 256
Database
ISI
SICI code
0040-4020(1998)54:1-2<243:AOTCOD>2.0.ZU;2-W
Abstract
Chiral 2-formyl and 2-(1-oxoalkyl)-1,3-dioxolanes have been prepared b y ozonolysis of the corresponding alkenes and by oxidation of 2-(1-hyd roxyalkyl)-1,3-dioxolanes, which are readily available from 2-(tributy lstannyl)dioxolanes, and taken through to alpha beta-unsaturated ester s by condensation with stabilized ylids. The -bis(ethoxycarbonyl)-1,3- dioxolan-2-yl]-2-pyridone 47 was prepared as an analogue of a (C)under -bar-nucleoside, but was found to be unstable. (C) 1997 Elsevier Scien ce Ltd. All rights reserved.