Phenanthrene synthesis: The synthesis of effusol a 9,10-Dihydrophenanthrene from the marsh grass Juncus effusus

Abstract

The synthesis of 5-ethenyl-1-methyl-9,10-dihydrophenanthrene-2,7-diol (effusol) (1), a natural product isolated from the marsh grass, Juncus effusus, is described. The key step was the intramolecular Ullmann reaction of methyl 2-bromo-3-[2'-(6''-bromo-3''-methoxy-2-methylphenyl)ethyl]-5-methoxybenzoate (19).