Highly Stereocontrolled Synthesis of 2,6-Dideoxy Sugars and its Application to Synthesis of Natural Products

Novel methodologies for stereocontrolled synthesis of 2,6-dideoxy sugars by efficient use of 2,6-anhydro-2-thio sugar and its application to synthesis of natural products are described. This article involves highly stereocontrolled and powerful glycosylations of 2,6-anhydro-2-thio sugar for synthesis of 2,6-dideoxy-α- and β-glycosides and highly sterecontrolled creations of C-3 configuration of 2,6-dideoxy sugar by an addition of a nucleophilic reagent to 2,6-anhydro-2-thio sugar. Further, the efficient total synthesis of erythromycin A, which is a most typical and clinically important macrolide antibiotic, from (9S)-9-dihydroerythronolide A is achieved by the successful application of the present novel methodologies.