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Stereoselective Synthesis of cis ‐Fused Perhydrofuro[2,3‐ b ]furan Derivatives from Sugar‐Derived Allyl Vinyl Ethers
Author(s) -
Sridhar Perali Ramu,
Reddy Gadi Madhusudhan,
Seshadri Kalapati
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200898
Subject(s) - chemistry , stereoselectivity , darunavir , furan , claisen rearrangement , ozonolysis , glycal , organic chemistry , vinyl ether , stereochemistry , catalysis , human immunodeficiency virus (hiv) , medicine , polymer , family medicine , antiretroviral therapy , viral load , copolymer
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.