Total synthesis of hydroxymethyl isonucleosides as potential antiviral agents

Abstract

Hydroxymethyl isodideoxynucleosides, designed as potential antiviral agents, have been synthesized through development of a multi-step procedure starting from furan and cyanovinyl acetate. Key steps in the synthesis include a Diels-Alder reaction, oxidative cleavage of alkene, a Mitsunobu reaction, stereospecific introduction of amino group and nucleobase construction.

Convenient Synthesis of Nucleoside and Isonucleoside Analogues

“…In this manner, the synthesis of nucleoside analogues in which the sugar and/or the heterocyclic moiety have been modified has received much attention as a consequence of their general biological activity and the potential use of such molecules as antiviral and antineoplasic therapeutic agents . In particular, isomeric nucleosides (isonucleosides) have revealed significant antiviral activities, and their syntheses are currently receiving much attention . In the past few years, we have developed new methods for the stereoselective synthesis of nucleosides by means of furanoid glycals 9 or 1,2-thiocarbonate sugars .…”