Synthetic Study of Mitchellene F by Intramolecular Diels-Alder Reaction

Mitchellenes, isolated from shrubs of the genus Eremophila in Australia, comprise a unique family of sesquiterpenoids, characterized by two, three, or four cyclic systems. The tricyclic mitchellene F was first reported by Greatrex in 2018. In pursuit of the total synthesis of mitchellene F, an intramolecular Diels-Alder reaction was found to be an efficient strategy, with an ortho-quinol intermediate obtained via the oxidation of the corresponding phenol. For the synthesis of this precursor phenol, a highly functionalized Grignard reagent was employed.