Synthesis of toxyloxanthone B

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 be...

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Bibliographic Details
Main Authors: Giallombardoa, Daniele, Nevin, Adam C., Lewis, William, Nawrat, Christopher C., Kitson, Russell R.A., Moody, Christopher J.
Format: Article
Published: Elsevier 2014
Online Access:https://eprints.nottingham.ac.uk/3298/
Description
Summary: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