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Journal of Chemical Crystallography

, Volume 43, Issue 11, pp 605–609 | Cite as

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

  • Pablo Labra-Vázquez
  • Margarita Romero-Ávila
  • Marcos Flores-Álamo
  • Martín A. Iglesias-Arteaga
Original Paper

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.

Keywords

Eschenmoser–Tanabe fragmentation 4,5-Seco-3-yn-5-oxosteroid X-ray diffraction NMR assignments 

Notes

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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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Pablo Labra-Vázquez
    • 1
  • Margarita Romero-Ávila
    • 1
  • Marcos Flores-Álamo
    • 1
  • Martín A. Iglesias-Arteaga
    • 1
  1. 1.Facultad de QuímicaUniversidad Nacional Autónoma de MéxicoMexicoMexico

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