Biomaterial Database

Steroids and related products. XLIII. The synthesis of 17-hydroxymethylprogesterone. 1977

C R Engel, and D Mukherjee

The synthesis of the first 17-hydroxymethyl analogue of a steroid hormone of the progesterone-corticoid group, 17-hydroxymethylprogesterone, is described. The starting material for its preparation was 3alpha,12alpha-diacetoxy-5beta-pregnan-20-one and the 17-hydroxymethyl structure was developed by functionalization of the 17-methyl group of a 17alpha-methyl etio ester by a Barton reaction. Neither 17-hydroxymethylprogesterone nor its acetate shows appreciable progestational activity in the Clauberg-McPhail assay.

UI	MeSH Term	Description	Entries
D008722	Methods	A series of steps taken in order to conduct research.	Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D011374	Progesterone	The major progestational steroid that is secreted primarily by the CORPUS LUTEUM and the PLACENTA. Progesterone acts on the UTERUS, the MAMMARY GLANDS and the BRAIN. It is required in EMBRYO IMPLANTATION; PREGNANCY maintenance, and the development of mammary tissue for MILK production. Progesterone, converted from PREGNENOLONE, also serves as an intermediate in the biosynthesis of GONADAL STEROID HORMONES and adrenal CORTICOSTEROIDS.	Pregnenedione,Progesterone, (13 alpha,17 alpha)-(+-)-Isomer,Progesterone, (17 alpha)-Isomer,Progesterone, (9 beta,10 alpha)-Isomer