Stereoselective synthesis of cis-fused perhydrofuro[2,3-b]furan derivatives from sugar-derived allyl vinyl ethers

摘要

A stereoselective methodology has been developed for the construction of cis-fused perhydrofuro[2,3-b]furans, via 3-C-branched glycal derivatives, involving Claisen rearrangement of sugar-derived allyl vinyl ethers, followed by a one-pot ozonolysis and acid-mediated acetalization. The methodology was used for the stereoselective synthesis of the P 2 ligand in the recently FDA approved HIV protease inhibitor darunavir (Prezista). The methodology was also successfully used for the synthesis of cis-fused perhydro-5-oxofuro[2,3-b] furan derivatives.