Accessing HIV-1 Protease Inhibitors through Visible-Light-Mediated Sequential Photocatalytic Decarboxylative Radical Conjugate Addition-Elimination-Oxa-Michael Reactions.
Tomislav KroloAditya BhattacharyyaAnd Oliver ReiserPublished in: Organic letters (2021)
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.
Keyphrases
- visible light
- antiretroviral therapy
- hiv positive
- hiv infected
- hiv testing
- human immunodeficiency virus
- hepatitis c virus
- acinetobacter baumannii
- hiv aids
- klebsiella pneumoniae
- men who have sex with men
- cancer therapy
- south africa
- quantum dots
- drug resistant
- escherichia coli
- molecularly imprinted
- cystic fibrosis
- electron transfer