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Kinetics of electrophilic fluorination of steroids and epimerisation of fluorosteroids

Rozatian, Neshat; Harsanyi, Antal; Murray, Ben J.; Hampton, Alexander S.; Chin, Emily J.; Cook, Alexander S.; Hodgson, David R.W.; Sandford, Graham

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Authors

Neshat Rozatian

Antal Harsanyi

Ben J. Murray

Alexander S. Hampton

Emily J. Chin

Alexander S. Cook

Graham Sandford



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, we conducted kinetics studies on enol ester derivatives of progesterone, testosterone, cholestenone and hydrocortisone with a series of electrophilic N−F reagents. We explored the stereoselectivities of fluorination reactions of progesterone enol acetate and the kinetic effects of additives, including methanol and water. The kinetics of epimerisation of 6β‐fluoroprogesterone to the more pharmacologically active 6α‐fluoroprogesterone isomer in HCl/acetic acid solutions are detailed.

Citation

Rozatian, N., Harsanyi, A., Murray, B. J., Hampton, A. S., Chin, E. J., Cook, A. S., …Sandford, G. (2020). Kinetics of electrophilic fluorination of steroids and epimerisation of fluorosteroids. Chemistry - A European Journal, 26(52), 12027-12035. https://doi.org/10.1002/chem.202001120

Journal Article Type Article
Acceptance Date Apr 8, 2020
Online Publication Date Aug 25, 2020
Publication Date 2020-09
Deposit Date Apr 2, 2020
Publicly Available Date Mar 28, 2024
Journal Chemistry - A European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 26
Issue 52
Pages 12027-12035
DOI https://doi.org/10.1002/chem.202001120

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Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/

Copyright Statement
© 2020 The Authors. Published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.





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