A Convenient Procedure for the Synthesis of 3β-Hydroxy-6-oxo-5α-steroids. Application to the Synthesis of Laxogenin

Authors

  • Martín A. Iglesias-Arteaga Universidad Nacional Autónoma de México
  • Eva M. Símuta-Lopez Benemérita Universidad Autónoma de Puebla
  • Sergio Xochihua-Moreno Benemérita Universidad Autónoma de Puebla
  • Omar Viñas-Bravo Benemérita Universidad Autónoma de Puebla
  • Sara Montiel Smith Benemérita Universidad Autónoma de Puebla
  • Socorro Meza Reyes Benemérita Universidad Autónoma de Puebla
  • Jesús Sandoval-Ramírez Benemérita Universidad Autónoma de Puebla

Keywords:

Laxogenin, diastereoselective epoxidation, 3β-hydroxy-6-oxo-5α-steroids

Abstract

Abstract. convenient pathway to obtain 3β-hydroxy-6-oxo-5α-steroids from 3β-acetoxy Δ5-steroids is reported; the methodology was applied to the synthesis of laxogenin (7), substance that behaves as a plant growth hormone. This is an alternative way to produce an important functionality found in many examples of naturally occurring steroids. The developed procedure uses inexpensive reagents and can be carried out in four steps. The oxidizing and acidic steps used in this methodology did not affect the labile spiroketal side chain present in diosgenin (16).

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Author Biographies

Martín A. Iglesias-Arteaga, Universidad Nacional Autónoma de México

Departamento de Química Orgánica, Facultad de Química

Eva M. Símuta-Lopez, Benemérita Universidad Autónoma de Puebla

Facultad de Ciencias Químicas

Sergio Xochihua-Moreno, Benemérita Universidad Autónoma de Puebla

Facultad de Ciencias Químicas

Omar Viñas-Bravo, Benemérita Universidad Autónoma de Puebla

Facultad de Ciencias Químicas

Sara Montiel Smith, Benemérita Universidad Autónoma de Puebla

Facultad de Ciencias Químicas

Socorro Meza Reyes, Benemérita Universidad Autónoma de Puebla

Facultad de Ciencias Químicas

Jesús Sandoval-Ramírez, Benemérita Universidad Autónoma de Puebla

Facultad de Ciencias Químicas

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Published

2020-08-07

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