NOVEL TOTAL SYNTHESIS OF THE 2-AZAANTHRAQUINONE ALKALOID SCORPINONE USING A TANDEM OXIDATION AND AZAELECTROCYCLIC REACTION

摘要

A new tandem oxidation and electrocyclic reaction of a 1-aza 6 pi-electron system derived from a known 3-hydroxynaphthalene derivative was developed for the synthesis of 2-azaanthraquinones. Total synthesis of scorpinone (1a) was achieved in seven steps using this new tandem reaction. In addition, the positional isomer, 7,9-dimethoxy-4-methylbenzo[g]isoquinoline-5,10-dione (1b) was also synthesized in the same way.