Total synthesis of hericene A featuring a CuBr2-mediated one-pot multi-step reaction

Hericenone family isolated from mushroom Hericium erinaceum shows diverse biological activities. We have investigated a practical route to 6-bromo-5,7-dihydroxyphthalide 5-methyl ether, a versatile intermediate in the synthesis of hericenones and related bioactive polyphenols. The synthesis features a combination of tandem Michael addition-Dieckmann condensation and CuBr2-mediated multi-step reactions. With this product in hand, total synthesis of hericene A (5'-deoxohericenone C), a leading polyphenol of this family, was achieved.