Collect. Czech. Chem. Commun. 1982, 47, 1240-1251
https://doi.org/10.1135/cccc19821240

Use of malonic acid derivatives for the construction of substituted side chains in the position 17β of steroids

Pavel Drašara, Vladimír Pouzara, Ivan Černýa, Miroslav Havela, Sofia N. Ananchenkob and Igor V. Torgovb

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
b Shemyakin Institute of Bioorganic Chemistry, USSR Academy of Sciences, Moscow 117 998, USSR

Abstract

Using the Knoevenagel reaction condensation products of 3β-acetoxyandrost-5-en-17-one with diethyl malonate, ethyl cyanoacetate and malononitrile were prepared which converted to derivatives of 3β-hydroxypregn-5-en-21-oic acid. Reductions and oxidations of the double bonds in the positions 5,6 and 17,20 and the stereochemistry at atoms C(17) and C(20) of some derivatives were also investigated. From derivatives of 23,24-dinorchola-5,17(20)-diene-21,22-diol compounds with a 1,3-dioxane ring in the side chain were prepared.