Collins, R.C., Paley, M.N., Tozer, G.M. et al. (1 more author) (2016) Synthesis of [3-C-13]-2,3-dihydroxy-4-methoxybenzaldehyde. Tetrahedron Letters, 57 (5). pp. 563-565. ISSN 0040-4039
Abstract
An efficient synthesis of [3-13C]-2,3-dihydroxy-4-methoxybenzaldehyde, an isotopically labelled probe of a common intermediate used in the synthesis of a number of biologically relevant molecules, has been achieved in 9 steps from an acyclic, non-aromatic precursor. A 13C label for molecular imaging was introduced in a linear synthesis from the reaction of [13C]-labelled methyl iodide with glutaric monomethyl ester chloride. Cyclisation then aromatisation gave 1,3-dimethoxybenzene and an additional methoxy group was introduced by a formylation/Baeyer–Villiger/hydrolysis/methylation sequence. Subsequent ortho-formylation and selective demethylation yielded the desired [3-13C]-2,3-dihydroxy-4-methoxybenzaldehyde.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Keywords: | Dynamic nuclear polarisation; C-13-Labelling; Baeyer-Villiger |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Medicine, Dentistry and Health (Sheffield) > Department of Infection, Immunity and Cardiovascular Disease The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Funding Information: | Funder Grant number BRITISH SOCIETY OF PAEDIATRIC ENDOCRINOLOGY AND DIABETES none |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 17 Mar 2016 12:29 |
Last Modified: | 19 Apr 2017 05:03 |
Published Version: | https://dx.doi.org/10.1016/j.tetlet.2015.12.088 |
Status: | Published |
Publisher: | Elsevier |
Identification Number: | 10.1016/j.tetlet.2015.12.088 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:96467 |