De novo asymmetric synthesis of homoadenosine via a palladium-catalyzed N-glycosylation.

ABSTRACT: [reaction: see text] A highly stereoselective synthesis of l-2-deoxy-beta-ribo-hexopyranosyl nucleosides from 6-chloropurine and Boc-protected pyranone has been developed. Our approach relies on the iterative application of a palladium-catalyzed N-glycosylation, diastereoselective reduction, and reductive 1,3-transposition. This strategy is amenable to prepare various natural and unnatural hexopyranosyl nucleosides analogues.

SUBMITTER: Guppi SR 

PROVIDER: S-EPMC2546502 | biostudies-literature | 2006 Jan

REPOSITORIES: biostudies-literature