SYNTHESIS OF NOVEL BICYCLIC NUCLEOSIDES RELATED TO NATURAL GRISEOLIC ACIDS

Abstract

Synthesis of novel, bicyclic nucleosides related to natural griseolic acids is described. The synthetic approach involves nucleobase construction at the C-2′ position of 1,4:3,6-diandydro-D-mannitol. The carbohydrate precursor used in the synthesis, 1,4:3,6-dianhydro-D-glucitol, can be prepared easily from D-glucitol. Bicyclic analogues of five naturally occurring nucleosides have been prepared. The single crystal X-ray structure of a representative example is presented and discussed.