Kinetics of Electrophilic Fluorination of Steroids and Epimerisation of Fluorosteroids.

ABSTRACT: Fluorinated steroids, which are synthesised by electrophilic fluorination, form a significant proportion of marketed pharmaceuticals. To gain quantitative information on fluorination at the 6-position of steroids, kinetics studies were conducted on enol ester derivatives of progesterone, testosterone, cholestenone and hydrocortisone with a series of electrophilic N-F reagents. The stereoselectivities of fluorination reactions of progesterone enol acetate and the kinetic effects of additives, including methanol and water, were investigated. The kinetics of epimerisation of 6β-fluoroprogesterone to the more pharmacologically active 6α-fluoroprogesterone isomer in HCl/acetic acid solutions are detailed.

SUBMITTER: Rozatian N 

PROVIDER: S-EPMC7540021 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature