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

Krolo, Tomislav and Bhattacharyya, Aditya and Reiser, Oliver (2021) Accessing HIV-1 Protease Inhibitors through Visible-Light-Mediated Sequential Photocatalytic Decarboxylative Radical Conjugate Addition-Elimination-Oxa-Michael Reactions. ORGANIC LETTERS, 23 (16). pp. 6283-6287. ISSN 1523-7060, 1523-7052

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Abstract

A photocatalytic decarboxylative radical conjugate addition-elimination-oxa-Michael reaction of hydroxyalkylated carboxylic acids with cyclopentenones is developed to construct diverse cyclopentanonyl-fused functionalized 5-7 membered cyclic ethers. 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 IC50 values.

Item Type: Article
Uncontrolled Keywords: DESIGN; STATE
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 07 Jul 2022 05:19
Last Modified: 07 Jul 2022 05:19
URI: https://pred.uni-regensburg.de/id/eprint/45827

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