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Access through your institution Buy or subscribe While the benzene ring remains ubiquitous in synthetic and medicinal chemistry, its flat, _sp_2-rich nature doesn’t always provide the best

framework to develop effective, bioavailable drugs. As such, saturated analogues have gained attention as benzene replacement groups, especially bridged cyclic structures like

bicyclo[1.1.1]pentanes (BCPs). Now, writing in _Angewandte Chemie_, Roman Bychek and Pavel Mykhailiuk from Enamine Ltd describe the development of a new method to access BCPs with a fluorine

substituent on one of the bridging carbon atoms. BCPs have a cyclobutane structure, with an additional methylene group bridging across two non-adjacent carbons. Their bicyclic structure

promotes their use in medicinal chemistry as benzene replacement groups compared to other saturated rings, such as cyclohexane, due to their small size and restricted flexibility. In the

decade since their first use as benzene bioisosteres, synthetic efforts have focussed on accessing BCPs with new substitution patterns, able to mimic the various derivatives of benzene rings

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calculated during checkout ADDITIONAL ACCESS OPTIONS: * Log in * Learn about institutional subscriptions * Read our FAQs * Contact customer support REFERENCES ORIGINAL ARTICLE * Bychek, R.

& Mykhailiuk, P. K. A practical and scalable approach to fluoro-substituted bicyclo[1.1.1]pentanes. _Angew. Chem. Int. Ed._ https://doi.org/10.1002/anie.202205103 (2022) Article  Google

Scholar  Download references AUTHOR INFORMATION AUTHORS AND AFFILIATIONS * Nature Reviews Chemistry http://www.nature.com/natrevchem/ Stephanie Greed Authors * Stephanie Greed View author

publications You can also search for this author inPubMed Google Scholar CORRESPONDING AUTHOR Correspondence to Stephanie Greed. RIGHTS AND PERMISSIONS Reprints and permissions ABOUT THIS

ARTICLE CITE THIS ARTICLE Greed, S. Taking fluorine to the bridge. _Nat Rev Chem_ 6, 447 (2022). https://doi.org/10.1038/s41570-022-00405-6 Download citation * Published: 27 June 2022 *

Issue Date: July 2022 * DOI: https://doi.org/10.1038/s41570-022-00405-6 SHARE THIS ARTICLE Anyone you share the following link with will be able to read this content: Get shareable link

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