We have developed and evaluated a new synthetic route for the synthesis of polycyclic 2-pyridone alkaloids, including azafluorenone and azaanthraquinone derivatives. The reaction sequence commences with an aldol condensation, followed by an alkene isomerization to a reactive pyrazinone intermediate prior to Diels-Alder cycloaddition with an alkyne dienophile. The resulting intermediate [2.2.2]diazabicyclic cycloadduct can undergo a base-promoted cycloreversion of one lactam bridging function. Application of this reaction sequence toward the synthesis of marcanine A, a natural product with potent anticancer potential, is also described.

New approach to polycyclic 2-pyridone alkaloids through a Diels-Alder/retro-Diels-Alder cycloaddition

256th National Meeting (2018)

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