Journal of the Chemical Society. Perkin transactions I p. 178 - 181 (1981)
Update date:2022-07-30
Topics: Magnesium Methoxide
Baker, S. Richard
Crombie, Leslie
Using the pyrone melt procedure of the preceding paper, 3,3',5,5'-tetrakismethoxycarbonylglaucyrone (2) and the tautomerically unsymmetrical 3'-acetyl-3,5,5'-trimethoxyglaucyrone (5) have been prepared.Conditions can be adjusted to prevent complete ester exchange in the reactin of 3,3'-diacetyl-5,5'-bisethoxycarbonylglaucyrone (1) with excess of magnesium methoxide, in accord with the mechanism proposed.On reaction with the latter reagent, the two new glaucyrones give aromatic penta-esters (11) and (14), and their mechanisms of formation are discussed.Heating these penta-esters effects cyclisation to xanthyrones having aromatic side-chain termini, (13) and (16), respectively.
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