METHODOLOGY FOR THE SYNTHESIS OF 3-OXYGENATED INGENANES - THE FIRST INGENOL ANALOGS WITH HIGH-AFFINITY FOR PROTEIN-KINASE-C

Previous work from our laboratories has demonstrated that the intramol ecular dioxenone photocycloaddition reaction leads to a stereoselectiv e synthesis of the carbocyclic ring system of the ingenane diterpenes with the ''inside-outside'' stereochemical relationship that is requir ed for biological activity. Two different approaches for the synthesis of C-3 oxygenated analogs of ingenol and the preparation of the first ingenane analog with high affinity for protein kinase C are described .