Natural products with 1,4-benzodioxin-based structures have demonstrated a wide variety of biological properties such as cytotoxic and hepatoprotective effects. The synthesis of a 3-benzyloxy-1,2-quinone has been carried out in a four-step process. Previous research in our lab shows that 1,4-benzodioxinscan be generated by an inverse electron demand hetero-Diels-Alder reaction of ortho-quinoneswith various enamines. Because only one of the regioisomers may demonstrate biological activities, a regioselective synthesis is desirable in the development. Our research is centered on attaining regioselectivity for the 1,4-benzodioxin through the aid of various metal ions. These efforts have been aided by DFT calculations on ground and transition states performed in the absence and presence of various metal ions. 

Regioselective 1,4-benzodioxin preparation through cycloaddition reactions

247th National Meeting (2014)

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