Regioselectivity in the thermal 1,2-cycloaddition of benzocyclobutenes to 3,4-dihydroisoquinolines

Abstract
Thermolysis of 1,2-dihydro-4,5-dimethoxybenzocyclobuten-1-ol (7a) in the presence of 3,4-dihydro-6,7-dimethyoxyisoquinoline (8), followed by reduction of the product with sodium borohydride, gave the berbine alkaloid xylopinine (2a). Regioselectivity in the cycloaddition of benzocyclobutenes to the 3,4-dihydroisoquinoline system is described.

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