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NMR Characterization and Crystal Structure of 22-Phenyl-3β-acetoxy-bisnorchol-5-en-22-one

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Abstract

Palladium catalyzed cross coupling between 3β-acetoxy-bisnorchol-5-en-22-oic acid and phenylboronic acid produced the hereto unknown 22-phenyl-3β-acetoxy-bisnorchol-5-en-22-one which crystallizes in the monoclinic system with space group P2 1 . The presence of 17β-substituent that bears both the C21 methyl group and the introduced phenylketone moiety provides a twisted conformation on C13–C14 for the D ring with asymmetry parameters (Altona et al., Tetrahedron 24:13–32, 1968): ∆ = 711.4, τm = 47.3 (2), ∆C2(C13–C14) = 5.7 (3), ∆Cs(C13) = 14.0 (3) and ∆Cs(C14) = 21.6 (3)°. The angle 77.20 (8)° between planes of the steroid-ABCD framework and phenyl ring evidences the relative orthogonal positions of these fragments. The 1H and 13C NMR characterization of the obtained compound are described.

Graphical Abstract

The crystal structure and NMR characterization of 22-phenyl-3β-acetoxy-bisnorchol-5-en-22-one are described.

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Acknowledgements

The authors acknowledge the financial support provided by Dirección General de Asuntos del Personal Académico (Project DGAPA-IN211714) and the Faculty of Chemistry-UNAM (PAPIIT-5000-9063). We want to express our gratitude to Dr. Carlos Cobas from Mestrelab® for assistance with the MestreNova NMR processing program and to Minerva Monroy-Barreto (USAI) for recording NMR spectra. Thanks are due to CONACYT-México for the scholarship granted to M.C.M-T.

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Authors and Affiliations

  1. Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510, Mexico, D.F., Mexico

    Martha C. Mayorquín-Torres, Marcos Flores-Álamo & Martin A. Iglesias-Arteaga

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  1. Martha C. Mayorquín-Torres
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  2. Marcos Flores-Álamo
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  3. Martin A. Iglesias-Arteaga
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Correspondence to Martin A. Iglesias-Arteaga.

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Mayorquín-Torres, M.C., Flores-Álamo, M. & Iglesias-Arteaga, M.A. NMR Characterization and Crystal Structure of 22-Phenyl-3β-acetoxy-bisnorchol-5-en-22-one. J Chem Crystallogr 44, 501–505 (2014). https://doi.org/10.1007/s10870-014-0539-x

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  • DOI: https://doi.org/10.1007/s10870-014-0539-x

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