Kinetics of electrophilic fluorination of steroids and epimerisation of fluorosteroids.
CHEMISTRY-A EUROPEAN JOURNAL(2020)
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 6 beta-fluoroprogesterone to the more pharmacologically active 6 alpha-fluoroprogesterone isomer in HCl/acetic acid solutions are detailed.
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Key words
epimerisation,fluorination,fluorosteroid,kinetics,stereoselectivity
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