Total Synthesis of Harringtonolide-Introducing Antidihydroxy Group and Forming the Lactone

Abstract

We reported a new relative stereochemical studies on the total synthesis of harringtonolide where the strategy relied upon the application of intermolecular Diels-Alder reaction (IMDA) to form the tricyclic skeleton proceeded very efficiently as we expected. Reductive-oxidation of the enolate was carried out with borane followed by hydrogen peroxide to give the desired crucial anti dihydroxy derivative. With the critical precursor in hand, the lactone was formed.