Accessing HIV-1 Protease Inhibitors through Visible-Light-Mediated Sequential Photocatalytic Decarboxylative Radical Conjugate Addition-Elimination–Oxa-Michael Reactions

09 June 2021, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


A novel photocatalytic decarboxylative radical conjugate addition-elimination-oxa-Michael reaction of hydroxyalkylated carboxylic acids with cyclopentenones has been developed to construct diverse cyclopentanonyl-fused functionalized cyclic ether derivatives in the presence of an inexpensive organic photocatalyst. The stereoselective synthetic strategy is amenable to substructural variation, establishing a direct total synthetic route to two diastereomers of C3-Amino cyclopentyltetrahydrofuranyl-derived potent HIV-1 protease inhibitors with low nanomolar IC 50 values.


Photoredox Catalysts
HIV 1 protease
Cyclopentanoyl fues cyclic ethers


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