| abstract |
The invention comprises a compound of the hydrochrysene series bearing a group selected from the groups of formyl, carboxyl and an alkoxycarbonyl group at 13-position and the process for preparing a hydrochrysene derivative bearing alkoxycarbonyl group at 13-position which comprises reducing a hydrochrysene derivative bearing a nitrile group at 13-position by an alkali aluminium hydride or its alkoxylated derivative in an organic solvent, hydrolysing the resulting imino compound by alkali hydroxide or alumina, oxidising the resulting aldehyde compound by chromic acid and esterifying the resulting carboxyl compound by diazoalkane in an organic solvent; similarly reducing an estra-1, 3, 5(10)-triene derivative bearing a nitrile group at 18-position or its alkoxylated derivative in an organic solvent and hydrolysing the resulting imino compound by alkali hydroxide or alumina gives the corresponding estra-1, 3, 5(10)-triene derivative bearing an oxo group in 18-position. The 17- or 20-oxo groups when present, in the reaction above, may be protected with ethylene or propylene glycol. The 18-oic acid compounds so obtained may be reduced at 18-position to a D-homo-androstan-17-one, said 17-oxo compound treated with a Grignard compound to obtain a 17b -methyl-17-ol compound, said 17-hydroxy compound dehydrated to obtain a 16, 17-unsaturated compound which is oxidised, e.g. with H2O2 to obtain a 3-acyloxy-pregnan-20-one. Specifications 873,019, 915,892, 936,892 and 959,799 are referred to. |