a
Facultad de Química, Universidad Nacional Autónoma de México, CDMX, 04510, México
› Author AffiliationsFinancial 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).
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.
2a Brassinosteroids: Chemistry, Bioactivity and Applications§#/ITL#§.
Cluter HG,
Yokota T,
Adam G.
ACS Symposium Series 474; American Chemical Society; Washington DC: 1991
12 Crystal data and experimental details of the structure determination are listed in the Supporting Information File (Table S1). CCDC 2103161 (14a), 2103162 (14b), and 2103163 (28) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
13
Horiuchi CA,
Haga A,
Satoh JY.
Bull. Chem. Soc. Jpn. 1986; 59: 2459
