Microbial synthesis of sex hormones

Estrone, which is obtainable from 19-hydroxycholesterol acetate through microbial oxidation, was chemically transformed to orally active estrogens, ethynylestradiol and methylestradiol. For progestin synthesis, $5{\alpha}$-bromo-619-oxidoisoandrosterone, was harvested from the culture broth(ATCC:19170), in which $5{\alpha}$-bromo-619-oxidocholestanol, acetate was added as a carbon source. Methylestrenolone, a potent orally active progestin, was synthesized from the harvested product via several reactions. Norethindrone, a popular progestin, was also prepared from 19-norandrostenedione. 19-Norandrostenedione is also available through microbial oxidation and chemical modification of $5{\alpha}$-chlor-619-oxidocholestanol, acetate.