Synthesis of toxyloxanthone B

Giallombardoa, Daniele and Nevin, Adam C. and Lewis, William and Nawrat, Christopher C. and Kitson, Russell R.A. and Moody, Christopher J. (2014) Synthesis of toxyloxanthone B. Tetrahedron, 70 (6). pp. 1283-1288. ISSN 0040-4020

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Abstract

A synthesis of the naturally occurring xanthone toxyloxanthone B is described, in which the key step is the regioselective addition of a methyl salicylate to a substituted benzyne followed by cyclization of the intermediate aryl anion to form the xanthone, the regiochemistry of the aryne addition being confirmed by X-ray crystallography. Subsequent introduction of the pyran ring by [3,3]-rearrangement and deprotection completed the synthesis

Item Type: Article
Additional Information: NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, 70(6), (2014), doi: 10.1016/j.tet.2013.12.055
Schools/Departments: University of Nottingham UK Campus > Faculty of Science > School of Chemistry
Identification Number: https://doi.org/10.1016/j.tet.2013.12.055
Depositing User: Moody, Prof Christopher
Date Deposited: 30 Jul 2014 11:57
Last Modified: 13 Sep 2016 12:45
URI: http://eprints.nottingham.ac.uk/id/eprint/3298

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