Synthesis of toxyloxanthone B

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

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

Citation

Giallombardoa, D., Nevin, A. C., Lewis, W., Nawrat, C. C., Kitson, R. R., & Moody, C. J. (2014). Synthesis of toxyloxanthone B. Tetrahedron, 70(6), https://doi.org/10.1016/j.tet.2013.12.055

• 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