Stereoselective Reduction of Steroidal 4-Ene-3-ketones in the Presence of Biomass-Derived Ionic Liquids Leading to Biologically Important 5β-Steroids

0583193 - ÚOCHB 2025 RIV US eng J - Journal Article
Szánti-Pintér, Eszter - Jirkalová, Lada - Pohl, Radek - Bednárová, Lucie - Kudová, Eva
Stereoselective Reduction of Steroidal 4-Ene-3-ketones in the Presence of Biomass-Derived Ionic Liquids Leading to Biologically Important 5β-Steroids.
ACS Omega. Roč. 9, č. 6 (2024), s. 7043-7052. ISSN 2470-1343. E-ISSN 2470-1343
R&D Projects: GA MŠMT(CZ) LX22NPO5104
Institutional support: RVO:61388963
Keywords : palladium-catalyzed hydrogenation * 3-oxo-4-ene steroids * nanoparticles
Impact factor: 4.1, year: 2022
Method of publishing: Open access
https://doi.org/10.1021/acsomega.3c08963

The stereoselective reduction of the steroidal 4-ene-3-ketone moiety (enone) affords the 5 beta-steroid backbone that is a key structural element of biologically important neuroactive steroids. Neurosteroids have been currently studied as novel and potent central nervous system drug-like compounds for the treatment of, e.g., postpartum depression. As a green methodology, we studied the palladium-catalyzed hydrogenation of steroidal 4-ene-3-ketones in the presence of ionic liquids derived from natural carboxylic acids. The hydrogenation proceeds with improved 5 beta-selectivity in the presence of tetrabutylammonium carboxylates as additives compared to the exclusive use of an organic solvent. Under optimal conditions, using tetrabutylammonium d-mandelate, the reduction of testosterone led to 5 beta-dihydrotestosterone in high yield and stereoselectivity and no byproduct formation was observed. Moreover, the catalyst could be recycled. The presence of additional substituents on the steroid backbone showed a significant effect on the 5 beta-selectivity.
Permanent Link: https://hdl.handle.net/11104/0351195