Mechanistic insights on the reactivity of furospirostanes with the 16β,22:22,25-diepoxy-23-acetoxymethyl-24-methyl side chain

Mariana Macías-Alonso; Marcos Flores-Álamo; Martín A Iglesias-Arteaga

doi:10.1016/j.steroids.2013.05.014

Mechanistic insights on the reactivity of furospirostanes with the 16β,22:22,25-diepoxy-23-acetoxymethyl-24-methyl side chain

Steroids. 2013 Sep;78(9):787-97. doi: 10.1016/j.steroids.2013.05.014. Epub 2013 May 23.

Authors

Mariana Macías-Alonso¹, Marcos Flores-Álamo, Martín A Iglesias-Arteaga

Affiliation

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

PMID: 23707575
DOI: 10.1016/j.steroids.2013.05.014

Abstract

F-ring opening in spirostanes with the 16β,22:22,25-diepoxy-23-acetoxymethyl-24-methyl side chain produces a Δ(22)-intermediate with an allylic acetoxy group. For this reason the reactivity profile of these compounds deviates from that observed in other naturally occurring or synthetic spirostanes and furospirostanes.

Keywords: Allylic substitution; Bromination; Bromodeacetoxylation; Elimination; Furospirostanes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Crystallography, X-Ray
Epoxy Compounds / chemical synthesis*
Epoxy Compounds / chemistry
Halogenation
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Spirostans / chemical synthesis*
Spirostans / chemistry

Substances

Epoxy Compounds
Spirostans