0000000001318087
AUTHOR
Adam C. Nevin
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 being confirmed by X-ray crystallography. Subsequent introduction of the pyran ring by [3,3]-rearrangement and deprotection completed the synthesis.
CCDC 973933: Experimental Crystal Structure Determination
Related Article: Daniele Giallombardo, Adam C. Nevin, William Lewis, Christopher C. Nawrat, Russell R. A. Kitson and Christopher J. Moody|2014|Tetrahedron|70|1283|doi:10.1016/j.tet.2013.12.055