A Novel Strategy for the Synthesis of Oxygenated Phenanthrenes Involving a Combination of Ullmann and McMurry Reactions.

A general synthetic procedure for the preparation of polyoxygenated phenanthrenes from substituted derivatives of benzaldehyde is described. The key compound is a 6,6'-biphenyl-1,1'-dicarboxaldehyde intermediate formed through an ambient temperature Ullmann coupling. The subsequent McMurry condensation gave rise to the phenanthrene in 45-57% yields.