Stereoselective Synthesis of cis‐Fused Perhydrofuro[2,3‐b]furan Derivatives from Sugar‐Derived Allyl Vinyl Ethers

Abstract

AbstractA 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 P2 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.