Stereospecific synthesis of (+) -cahbocyclic 2'-deoxyadenosine. an improved procedure for the preparation of (+)-(1r,2s,4r)-4-amino-2-hydroxy-1-hydroxymethylcyclopentane.

Abstract

An improved procedure for the preparation of a versatile synthetic precursor, (+)- 13, of carba-2'-deoxyribonucleosides and the first stereospecific way to enantiomerically pure carbocyclic 2'-deoxyadenosine, (+)- 14, are presented from bicyclic lactone diol (+)- 1. An unexpected formation of the disubstituted 2-oxabicyclo[2.2.1]heptane skeleton 15 through a hypervalent iodo species derived from 6 is also reported.