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.
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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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