Collect. Czech. Chem. Commun. 1996, 61, 276-287

Partial Modifications of Hydroxy Groups in 5-Methyl-5β-estr-9-ene Derivatives

Alexander Kasal and Miloš Buděšínský

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


In compounds of the Westphalen type the substituent in position 6 has been removed: the 6β-hydroxyl in 3β,17β-dibenzoyloxy-5-methyl-5β-estr-9-en-6β-ol (1) by oxidation to ketone 2 and Huang Minlon reduction, the 6β-chlorine atom in 3β-acetoxy-6β-chloro-5-methyl-5β-estr-9-en-17-one (13) by reduction with tributyltin hydride. Androstenedione, testosterone and methyltestosterone analogues 4, 5, and 16, respectively, were prepared from 3β,17β-dihydroxy-5-methyl-5β-estr-9-ene (3) by partial oxidation or partial acylation followed by oxidation. Alternatively, these derivatives were prepared from compound 13 without the need of partial transformations.

Keywords: Steroids; Conformational analysis; Hormone analogues.