Synthesis of (±)-E-4-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)-but-3-en-2-one: A novel degraded carotenoid isolated from New Zealand thyme (Thymus vulgaris) honey

Article abstract of DOI:10.1016/S0040-4039(00)79850-9

A racemic synthesis of the title compound is described starting from β-ionone. The key steps involve selective hydroboration of a triene, followed by molybdenum mediated epoxidation of the resulting homoallylic alcohol with subsequent ring opening of the epoxide to give the title compound.