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Synthesis 2022; 54(03): 643-654
DOI: 10.1055/a-1647-7610
DOI: 10.1055/a-1647-7610
feature
Synthesis and Characterization of Hybrid Dimeric Steroid Spiroketals
Financial support was provided by Dirección General de Asuntos del Personal Académico (Project DGAPA-IN218820), Consejo Nacional de Ciencia y Tecnología (Project A1-S-8019), Facultad de Química, Universidad Nacional Autónoma de México (PAIP-5000-9063), and the Ministry of Education, Youth and Sports of the Czech Republic through the e-INFRA CZ (ID:90140).
Abstract
The synthesis of six dimeric spiroketals bearing an estradiol half fused to the 5α- or 5β-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.
Key words
Sonogashira coupling - Pd-catalyzed spiroketalization - hybrid steroid dimers - NMR - X-ray diffraction - DFT-NBO calculationsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1647-7610.
- Supporting Information
Publication History
Received: 14 August 2021
Accepted after revision: 17 September 2021
Accepted Manuscript online:
17 September 2021
Article published online:
27 October 2021
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For reviews, see:
For additional antitumor hybrid dimers, see: