Stereocontrolled synthesis of novel 6 '(alpha)-hydroxy carbovir analogues

Abstract

This paper describes the racemic and stereoselective synthetic route for a novel 6'(alpha)-hydroxy-carbovir from a simple acyclic precursor. Solketal. The relative stereochemistry of the target nucleosides was successfully controlled by a sequential stereoselective glycolate Claisen rearrangement followed by a ring-closing metathesis (RCM). Adenine and cytosine were coupled using a Pd(0) catalyzed allylic alkylation strategy in a high regio- and stereoselective manner. (C) 2003 Elsevier Ltd. All rights reserved.