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Synthesis of toxyloxanthone B

Giallombardoa, Daniele; Nevin, Adam C.; Lewis, William; Nawrat, Christopher C.; Kitson, Russell R.A.; Moody, Christopher J.

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Authors

Daniele Giallombardoa

Adam C. Nevin

William Lewis

Christopher C. Nawrat

Russell R.A. Kitson

Christopher J. Moody



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

Journal Article Type Article
Publication Date Jan 1, 2014
Deposit Date Jul 30, 2014
Publicly Available Date Jul 30, 2014
Journal Tetrahedron
Print ISSN 0040-4020
Electronic ISSN 0040-4020
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 70
Issue 6
DOI https://doi.org/10.1016/j.tet.2013.12.055
Public URL https://nottingham-repository.worktribe.com/output/998541
Publisher URL http://www.sciencedirect.com/science/article/pii/S0040402013019236
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

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