Catalysis

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

Oliver Reiser Universität Regensburg

Abstract

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.

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Version V1

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