Model studies toward the synthesis of the bioactive diterpenoid, harringtonolide

In model studies towards the synthesis of harringtonolide, the construction of the tropone moiety via arene cyclopropanation was investigated. The installation of the lactone ring was accomplished by way of a Diels-Alder cycloaddition of various indenones and α-pyones. The incorporation of the key bridge methyl group and subsequent control of its stereochemistry is also outlined.