A new synthesis of (±)-carbocyclic 2′-deoxyuridines

✍ Scribed by P. Ravenscroft; R.F. Newton; D.I.C. Scopes; C. Williamson

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 125 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)84090-3

✦ Synopsis

±)-Carbocyclic 2'-deoxyuridine (la) and its (E)-5-(2-bromovinyl) derivative (lb) have been synthesized in B steps from (la,3a,5a)-6-oxabicyclo[3.1.0]hexan-3-o1 (2).

Carbocyclic analogues of nucleosides are attracting increasing attention as potential antiviral agents.

For example, cyclaradine (carbocyclic arabinofuranosyladenine) inhibits the replication of herpes simplex virus (HSV) types 1 and 2, and its 5'-methoxyacetate prodrug exhibits significant efficacy in the treatment of genital herpes in guinea pigs 1• Carbocyclic 5-halo 2and (~)-5-( 2-bromovinyl) 3, '+-2'deoxyuridines also possess good activity in vitro against HSV-l. The latter class of compounds are prepared from (±)-carbocyclic 2'-deoxyuridine (1a) or its 3' ,5'-diace~ate derivative. However, the existing synthesis of (1a) is non-regiospecific and requires separation of positional isomers at an early stage of the synthetic sequence 5,6.