GB756434A - Steroids - Google Patents

Abstract

Steroids (including D-homosteroids) having an 11-methylene group are oxygenated by subjecting them to treatment with oxygenating substances produced by growing a fungus of the genus Neurospora, e.g. N. sitophila, N. crassa, N. tetrasperma and their mutants, under aerobic conditions in the presence of a fermentation medium containing assimilable non-steroidal carbon, e.g. carbohydrates. Additionally the fermentation medium requires assimilable nitrogen and phosphate. Suitable starting materials are progesterone, 17-hydroxy-progesterone, 17a -progesterone, testosterone, pregnenolones, 3b -hydroxy-5,16-pregnadien-20-one, pregnenolone acetate, 3-hydroxy-5,6-oxidopregnan-20-one, 3-hydroxy-5-chloro-pregnan-20 - one, 5,6 - oxidopregnane - 3,20 - dione, 4 - bromo- and 4-chloro-pregnane-3,20-dione, 5-chloro - pregnane - 3,20 - dione, 3 - ketopregnan-20 - ol, 3 - keto - allopregnan - 20 - ol, 3b - hydroxy - 16,17 - oxido - 21 - acetoxy - 5 - pregnen - 20 - one, 3b - hydroxy - 16,17 - oxido - 5 - pregnen - 20 - one, 3b - hydroxy - 5,6,21 - tribromo - 16,17 - oxidopregnan - 20 - one, 3b - hydroxy - 16 - bromo - 17 - hydroxy - 5 - pregnen - 20 - one, 3b - hydroxy - 16 - chloro - 17 - hydroxy - 5 - pregnen - 20 - one, 3b - hydroxy - 5(6),16(17) - dioxidopregnan - 20 - one and the 21-bromo-, 21-acetoxy- and 21-hydroxy derivatives thereof, 11 - desoxycorticosterone, 11 - desoxycorticosterone - 17 - ol and acyloxy derivatives, 21-hydroxypregnenolone and acyloxy derivatives, 17,21-dihydroxypregnenolone and 17,21-acyloxy derivatives thereof, 4- or 5-androsten - 3 - ol - 17 - one and 3 - esters thereof, ergosterol, stigmasterol, stigmastanol and 3-esters thereof, stigmastenone, stigmastanone, cholestenone, cholic acid, desoxycholic acid, lithocholic acid, cholanic acid, norcholanic acid, bisnorcholanic acid, cholenic acid, norcholenic acid, bisnorcholenic acid and esters thereof, 10-normethyl, 13-normethyl and 10,13-bisnormethyl steroids, D-homo-4-androstene-3,17a - dione, D - homotestosterone, D - homo - 17a,a - methyltestosterone, D - homo - 17a,b - methyltestosterone, 17a-methyl-17a-hydroxy-D - homo - 4 - androstene - 3,17 - dione, and their 4,5-dihydro, ring A saturated analogues, D - homo - androstenones, and D - homo - epidehydroandrosterone. As nutritional essentials for the media, there may be used p-amino-benzoic acid, choline, inosital, niacin, pantothenic acid, pyridoxine, riboflavin, thiamin, arginine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, threonine, tryptophane and valine. Examples disclose the oxygenation of progesterone, 17a - hydroxyprogesterone, 17a ,21 - dihydroxyprogesterone, pregnane - 3,20 - dione, 21 - hydroxy - 4 - pregnene - 3,20 - dione, and 16-dehydroprogesterone.