Synthesis and Characterization of Hybrid Dimeric Steroid Spiroketals

0549377 - ÚFCH JH 2023 RIV DE eng J - Článek v odborném periodiku
Mayorquín-Torres, M. C. - Maldonado-Domínguez, Mauricio - Flores-Álamo, M. - Iglesias-Arteaga, M. A.
Synthesis and Characterization of Hybrid Dimeric Steroid Spiroketals.
Synthesis. Roč. 54, č. 03 (2022), s. 643-654. ISSN 0039-7881. E-ISSN 1437-210X
Výzkumná infrastruktura: e-INFRA CZ - 90140
Institucionální podpora: RVO:61388955
Klíčová slova: reduction * Sonogashira coupling * Pd-catalyzed spiroketalization * hybrid steroid dimers * nmr * X-ray diffraction * DFT-NBO calculations
Obor OECD: Physical chemistry
Impakt faktor: 2.6, rok: 2022
Způsob publikování: Omezený přístup
https://www.thieme-connect.de/products/ejournals/abstract/10.1055/a-1647-7610

The synthesis of six dimeric spiroketals bearing an estradiol half fused to the 5 alpha- or 5 beta-epimers of androstane, cholestane, and spirostane nuclei is described. The synthetic procedure comprises the Sonogashira- coupling of different steroid alkynes with 2-iodoestradiol 17-monoacetate, followed by Pd-catalyzed spiroketalization. The structural characterization of the obtained hybrid dimers was performed using a combination of 1D and 2D NMR techniques, and was assisted by DFT calculations. Single crystal X-ray diffraction of one of the obtained compounds confirmed the proposed structures.
Trvalý link: http://hdl.handle.net/11104/0325386