A CONVENIENT SYNTHESIS OF RACEMIC 2'-DEOXY CARBOCYCLIC THYMIDINES LACKING THE 5'-METHYLENE GROUP

Authors
ZHOU JL SHEVLIN PB
Citation
Jl. Zhou et Pb. Shevlin, A CONVENIENT SYNTHESIS OF RACEMIC 2'-DEOXY CARBOCYCLIC THYMIDINES LACKING THE 5'-METHYLENE GROUP, Tetrahedron letters, 39(46), 1998, pp. 8373-8376
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
46
Year of publication
1998
Pages
8373 - 8376
Database
ISI
SICI code
0040-4039(1998)39:46<8373:ACSOR2>2.0.ZU;2-V
Abstract
A convenient synthesis of racemic 2'-deoxy carbocyclic thymidines lack ing the 5'-methylene group is reported. Thus, appropriately protected nucleic acid bases are coupled to 3-cyclopentenol, 1, via the Mitsunob u reaction. Epoxidation of the protected thymine substituted cyclopent ene gives the corresponding syn and anti-epoxides in a 4:1 ratio. Ring opening of the syn-epoxide by a variety of nucleophiles leads to the racemic 2'-deoxy carbocyclic thymidines lacking the 5'-methylene group . (C) 1998 Elsevier Science Ltd. All rights reserved.