Oxetane Synthesis via Alcohol C–H Functionalization

Paul, Subhasis; Filippini, Dario; Ficarra, Filippo; Melnychenko, Heorhii; Janot, Christopher; Silvi, Mattia

Abstract

Oxetanes are strained heterocycles with unique properties that have triggered significant advances in medicinal chemistry. However, their synthesis still presents significant challenges that limit the use of this class of compounds in practical applications. In this Letter, we present a methodology that introduces a new synthetic disconnection to access oxetanes from native alcohol substrates. The generality of the approach is demonstrated by the application in late-stage functionalization chemistry, which is further exploited to develop a single-step synthesis of a known bioactive synthetic steroid derivative that previously required at least four synthetic steps from available precursors.

• Journal Article Type: Article
• Acceptance Date: Jul 18, 2023
• Online Publication Date: Jul 18, 2023
• Publication Date: Jul 26, 2023
• Deposit Date: Jul 26, 2023
• Publicly Available Date: Jul 26, 2023
• Journal: Journal of the American Chemical Society
• Print ISSN: 0002-7863
• Electronic ISSN: 1520-5126
• Publisher: American Chemical Society (ACS)
• Peer Reviewed: Peer Reviewed
• Volume: 145
• Issue: 29
• Pages: 15688–15694
• DOI: https://doi.org/10.1021/jacs.3c04891
• Keywords: Alcohols, Chemical reactions, Cyclization, Irradiation, Organic polymers
• Public URL: https://nottingham-repository.worktribe.com/output/23220604
• Publisher URL: https://pubs.acs.org/doi/10.1021/jacs.3c04891