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Synthesis, Crystal Structure and NMR Assignments of 17β-Acetoxy-4,5-secoandrost-3-yn-5-one

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Abstract

The synthesis, crystal structure and NMR characterization of 17β-acetoxy-4,5-secoandrost-3-yn-5-one (3) are described. The title compound which crystallizes in the orthorhombic system with a space group P212121, was obtained by Eschenmoser–Tanabe fragmentation of the mixture of epimeric epoxides 17β-acetoxy-4,5-epoxy-5α-androstan-3-one (2a) and 17β-acetoxy-4,5-epoxy-5β-androstan-3-one (2b).

Graphical Abstract

The synthesis, crystal structure and NMR assignments of 17β-acetoxy-4,5-secoandrost-3-yn-5-one is described.

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Acknowledgments

The authors thank to Dirección General de Asuntos del Personal Académico (DGAPA-UNAM) for financial support via Project IN221911-3. Thanks are due to Rosa I. del Villar Morales, Georgina Duarte Lisci (USAI-UNAM) for recording NMR and MS spectra. We want to express our gratitude to Dr. Carlos Cobas from Mestrelab® for assistance with the MestreNova NMR processing program.

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Authors and Affiliations

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

    Pablo Labra-Vázquez, Margarita Romero-Ávila, Marcos Flores-Álamo & Martín A. Iglesias-Arteaga

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  1. Pablo Labra-Vázquez
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  2. Margarita Romero-Ávila
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  3. Marcos Flores-Álamo
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  4. Martín A. Iglesias-Arteaga
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Correspondence to Martín A. Iglesias-Arteaga.

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Labra-Vázquez, P., Romero-Ávila, M., Flores-Álamo, M. et al. Synthesis, Crystal Structure and NMR Assignments of 17β-Acetoxy-4,5-secoandrost-3-yn-5-one. J Chem Crystallogr 43, 605–609 (2013). https://doi.org/10.1007/s10870-013-0466-2

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  • DOI: https://doi.org/10.1007/s10870-013-0466-2

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