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Janus all-cis 2,3,4,5,6-pentafluorocyclohexyl building blocks applied to medicinal chemistry and bioactives discovery chemistry

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Date
17/11/2021
Author
Clark, Joshua
Neyyappadath, Rifahath M.
Yu, Cihang
Slawin, Alexandra M. Z.
Cordes, David B.
O'Hagan, David
Keywords
Organofluorine chemistry
Janus motif
Aryl hydrogenation
Organic chemistry
Fluorocyclohexanes
QD Chemistry
QH301 Biology
R Medicine
DAS
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Abstract
Monoalkylated derivatives of the unusually polar all- cis 2,3,4,5,6- pentafluorocyclohexyl (Janus face) motif are prepared starting from an aryl hydrogenation of 2,3,4,5,6- pentafluorophenylacetate methyl ester 15 . The method used Zeng's Rh(CAAC) carbene catalyst 4 in the hydrogenation following the protocol developed by Glorius. The resultant Janus pentafluorocyclohexylacetate methyl ester 16 was converted to the corresponding alcohol 18 , aldehyde 13 , bromide 29 and azide 14 through functional group manipulations, and some of these building blocks were used in Ugi-multicomponent and Cu-catalysed click reactions. NBoc protected pentafluoroarylphenylalanine methyl ester 35 was also subject to an aryl hydrogenation, and then deprotection to generate the Janus face ß-pentafluorocyclohexyl-alanine amino acid 15 , which was incorporated into representative members of an emerging class of candidate antiviral compounds. Log P measurements demonstrate that the all- cis 2,3,4,5,6-pentafluorocyclohexyl ring system is more polar than a phenyl ring. In overview the paper introduces new building blocks containing this Janus ring and demonstrates their progression to molecules typically used in bioactives discovery programmes.
Citation
Clark , J , Neyyappadath , R M , Yu , C , Slawin , A M Z , Cordes , D B & O'Hagan , D 2021 , ' Janus all- cis 2,3,4,5,6-pentafluorocyclohexyl building blocks applied to medicinal chemistry and bioactives discovery chemistry ' , Chemistry - A European Journal , vol. 27 , no. 64 , 202102819 , pp. 16000-16005 . https://doi.org/10.1002/chem.202102819
Publication
Chemistry - A European Journal
Status
Peer reviewed
DOI
https://doi.org/10.1002/chem.202102819
ISSN
0947-6539
Type
Journal article
Rights
Copyright © 2021 The Authors. Chemistry - A European Journal 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.
Description
We thank EPSRC for a grant (EP/R013799/1) and Studentships (JLC) through the EPSRC CRITICAT CDT programme and also the Chinese Scholarship Council (CY).
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/24093

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