Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 52, Pages 12027-12035Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001120
Keywords
epimerisation; fluorination; fluorosteroid; kinetics; stereoselectivity
Categories
Funding
- Faculty of Science, Durham University
- European Community
- EFPIA [115360]
- Durham University
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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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