A facile and simple entry into isodideoxynucleosides

Abstract

Sharpless asymmetric dihydroxylations of homoallylic alcohol derivative 3 with AD mix-α afforded α addition product 4a predominantly. Compound 4a was produced with very high selectivity when 3 was treated with AD mix-β. The inherent hydroxylic functionalities of 4a were judiciously exploited to develop a simple and efficient synthesis of (3′S,5′S)-isodideoxynucleosides. I and II are two representative target molecules for our synthesis in this regard.