Synthesis of Progesterone

Synthesis of Progesterone

Progesterone is the main pro-gestational steroid hormone secreted by the corpus luteum in the ovary (female reproductive system). It plays an important roles in the menstrual cycle and in maintaining the early stages of pregnancy. Progesterone levels steadily rise throughout pregnancy, reaching their highest levels in the third trimester. Low progesterone levels during pregnancy can lead to complications like Spotting or bleeding, Miscarriage, Ectopic pregnancy, Preterm labor etc.

Biosynthesis of Progesterone

Progesterone can biosynthesizes from Cholesterole and from Stigmasterol acetate. Both biosynthesis are given below-

Biosynthesis of Progesterone from Cholesterol

Chlolesterol on treatment with aceticanhydride and bromine yielding dibromo derivative, which on oxidation followed by debromination yields dehydroepiandrosterone. One carbon of chain was introduced by treatment with HCN. Grignard reaction and selective hydrogenation of the conjugated double bond affords pregnenolone which on Oppenauer oxidation give progesterone.

Biosynthesis of Progesterone from Stigmasterol acetate

Stigmasterol acetate on Bromination followed by ozonization and debromination yields acetylbisnorcholenic acid, which on reaction with Grignard reagent yields diphenylethylene derivative. Bromination followed by oxidation, debromination and hydrolysis yields pregnenolone. Oppeneauer oxidation of pregnenolone yields progesterone.