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A stepwise lactol carbocyclisation to bridged ethers via a keto–acetal cascade

McCarthy, S; Marson, CM; (2022) A stepwise lactol carbocyclisation to bridged ethers via a keto–acetal cascade. Journal of Chemical Research , 46 (1) pp. 1-8. 10.1177/17475198221079498. Green open access

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Abstract

Lactol carbocyclisations provide a succinct method of constructing the oxabicyclo[3.2.1]octane scaffold, a motif present in various natural products of medicinal interest. Lactols containing an unsaturated ketone or ester were prepared by olefin cross-metathesis; an electrophilic alkene derived from methyl vinyl ketone underwent concomitant terminal α-methylenation and oxa-Michael addition to give a bridged lactol which then underwent oxygen-to-carbon transposition in the presence of titanium (IV) chloride giving the desired unsaturated carbocyclic seven-membered bridged ether via a novel dehydrative cascade considered to involve titanium enolates.

Type: Article
Title: A stepwise lactol carbocyclisation to bridged ethers via a keto–acetal cascade
Open access status: An open access version is available from UCL Discovery
DOI: 10.1177/17475198221079498
Publisher version: https://doi.org/10.1177%2F17475198221079498
Language: English
Additional information: This article is distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 License (https://creativecommons.org/licenses/by-nc/4.0/) which permits non-commercial use, reproduction and distribution of the work without further permission provided the original work is attributed as specified on the SAGE and Open Access pages (https://us.sagepub.com/en-us/nam/open-access-at-sage).
Keywords: Bridged ether synthesis, dehydrative rearrangement, enone–lactol cyclisation, keto–acetal cascade, oxa-Michael acetal formation
UCL classification: UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL
URI: https://discovery.ucl.ac.uk/id/eprint/10145924
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