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- W2961639602 abstract "We describe here the syntheses of optically pure (3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-ol and (3aR,4R,7aS)-hexahydro-4H-furo[2,3-b]pyran-4-ol. These stereochemically defined heterocycles are important high-affinity P2 ligands for a variety of highly potent HIV-1 protease inhibitors. The key steps involve an efficient Paterno-Buchi [2 + 2] photocycloaddition, catalytic hydrogenation, acid-catalyzed cyclization to form the racemic ligand alcohol, and an enzymatic resolution with immobilized Amano Lipase PS-30. Optically active ligands (-)-6 and (+)-6 were obtained with high enantiomeric purity. Enantiomer (-)-6 has been converted to potent HIV-1 protease inhibitor 3." @default.
- W2961639602 created "2019-07-23" @default.
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- W2961639602 date "2019-07-16" @default.
- W2961639602 modified "2023-09-26" @default.
- W2961639602 title "A Photochemical Route to Optically Active Hexahydro-4<i>H</i>-furopyranol, a High-Affinity P2 Ligand for HIV-1 Protease Inhibitors" @default.
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- W2961639602 doi "https://doi.org/10.1021/acs.joc.9b01361" @default.
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