Synthesis of 3-methyl-3-hydroxy-6-oxo-androstane derivatives

Hana Chodounská; Vladimír Pouzar; Milos Budesínský; Barbora Slavíková; Ladislav Kohout

doi:10.1016/j.steroids.2004.04.007

Synthesis of 3-methyl-3-hydroxy-6-oxo-androstane derivatives

Steroids. 2004 Sep;69(10):605-12. doi: 10.1016/j.steroids.2004.04.007.

Authors

Hana Chodounská¹, Vladimír Pouzar, Milos Budesínský, Barbora Slavíková, Ladislav Kohout

Affiliation

¹ Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic.

PMID: 15465104
DOI: 10.1016/j.steroids.2004.04.007

Abstract

3alpha,17beta-Dihydroxy-3beta-methyl-5alpha-androstan-6-one (1) and 3beta,17beta-dihydroxy-3alpha-methyl-5alpha-androstan-6-one (13) were prepared by the reaction of methylmagnesium bromide with the 3-ketosteroids. Structures and configurations in position 3 were determined by NMR spectra. Substitution in the position 6 influences the ratio of the products.

Publication types

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

MeSH terms

Androstane-3,17-diol / analogs & derivatives*
Androstane-3,17-diol / chemical synthesis
Androstane-3,17-diol / chemistry
Androstanes / chemical synthesis*
Androstanes / chemistry
Androstenediol / chemistry
Ketosteroids / chemistry
Magnetic Resonance Spectroscopy
Methylation
Molecular Conformation
Molecular Structure

Substances

Androstanes
Ketosteroids
Androstane-3,17-diol
Androstenediol
androstane