Journal
ORGANIC LETTERS
Volume 23, Issue 16, Pages 6283-6287Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01964
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Funding
- Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) [TRR 325444632635-A2]
- European Union [795161]
- Marie Curie Actions (MSCA) [795161] Funding Source: Marie Curie Actions (MSCA)
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A photocatalytic reaction was developed for constructing diverse cyclopentanonyl-fused cyclic ethers, serving as a direct synthetic route to potent HIV-1 protease inhibitors with low nanomolar IC50 values.
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.
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