Synthesis and Optical Resolution of (±)10,11-Dihydroxy-5H-dibenzo[a,d]cyclohepten-5-one

Synthesis and Optical Resolution of (±)10,11-Dihydroxy-5H-dibenzo[a,d]cyclohepten-5-one

The synthesis and resolution of ($\pm$)-10,11-dihydroxydibenzosuberenone 3, a potential pharmaceutical compound, is described. It was synthesized from the 5H-dibenzo[a,d]cycloheptene-5-one (dibenzosuberenone) 1, and converted to diastereomeric isomers using (R)-(+)-$\alpha$-methylbenzylamine. Optical resolution of ($\pm$)-10,11-dihydroxydibenzosuberenone 3 was possible by fractional recrystallization of the diastereomer formed in ethanol. The optical resolution of 10,11-dihydroxydibenzosuberenone through formation of its phosphoamidates 5 using the (R)-(+)-$\alpha$-methylbenzylamine was achieved. These compounds provided the optical rotation of [${\alpha}]=-64.3$ for (-)-10,11-dihydroxy-dibenzosuberenone and [${\alpha}]=+61.3$ for (+)-10,11-dihydroxydibenzosuberenone. The (-)- and (+)-enantiomers were prepared in five steps from dibenzosuberenone with overall yields of 11.66% and 9.38%, respectively.