Synthesis of 3-methyl-3-hydroxy-6-oxo-androstane derivatives.
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.
Chodounská
Hana
H
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic.
Pouzar
Vladimír
V
Budesínský
Milos
M
Slavíková
Barbora
B
Kohout
Ladislav
L
D015113:Androstane-3,17-diol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000731:Androstanes / Q000138:chemical synthesis* / Q000737:chemistry; D015114:Androstenediol / Q000737:chemistry; D007664:Ketosteroids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008968:Molecular Conformation; D015394:Molecular Structure
D000731:Androstanes; D007664:Ketosteroids; D015113:Androstane-3,17-diol; D015114:Androstenediol; C033936:androstane