Total Synthesis of Cycloaraneosene, a Fundamental Hydrocarbon of "epi"-Fusicoccane Diterpenoids, and the Structure Revision of Its Congener, Hydroxycycloaraneosene

Article abstract of DOI:10.1246/cl.1986.1989

The 5-8-5-membered tricyclic diterpene, cycloaraneosene, has been totally synthesized via the stereoselective condensation of two units of optically active iridoids, Cope rearrangement and chemical reduction of the tetrasubstituted C=C bond.The NMR spectrum of synthetic 9α-hydroxycycloaraneosene was not identical with the congener product, and the natural alcohol is likely to be 8β-hydroxyl derivative.