Tandem Benzyne Cycloadditions Leading to Polycyclic Compounds

Abstract

Deoxykojic acid (1) reacts with two benzyne molecules to afford 9-methyl-7-phenoxy-5,9-dihydro-5,9-epoxy-6H-benzocyclohepten-6-one (2) in 33% yield. Maltol (5) reacts with three molecules of benzyne to afford (4bα,5β,10β,11aα)-10-methyl-11a-phenoxy-4b,5,10,11a-tetrahydro-5,10-epoxy-11H- benzo[a]benzo[3,4]cyclobuta[1,2-d]cyclohepten-11-one (6a) in 36% yield.