Synthesis of Aromatic Compounds Using Combinations of Ring-Closing Olefin Metathesis, Dehydration, Oxidation, and Tautomerization

An approach to aromatic compounds using combinations of ring-closing olefin metathesis (RCM), dehydration, oxidation, and tautomerization is reported. The RCM reaction of 1,7-diene-3,5-diols, which were readily prepared by the allylation of aldol products, gave corresponding cyclized products, 4-cyclohexene-1,3-diols, in high yields. The subsequent dehydration or oxidation of 4-cyclohexene-1,3-diols led to versatile substituted benzenes including phenol and resorcinol derivatives.