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.
Giallombardo, D., Nevin, A.C., Lewis, W., Nawrat, C.C., Kitson, R., Moody, C.J. (2014). Synthesis of toxyloxanthone B. TETRAHEDRON, 70(70), 1283-1288 [http://dx.doi.org/10.1016/j.tet.2013.12.055].
Synthesis of toxyloxanthone B
GIALLOMBARDO, Daniele;
2014-01-01
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.
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