Biomimetic approach to the synthesis of the tricyclic diterpene, sarcoglane

ORGN 566

Ryan A. Sowers, Alexander J Reif, and Eduard Casillas, eduard.casillas@villanova.edu. Department of Chemistry, Villanova University, 800 E. Lancaster Ave., Villanova, PA 19085

Sarcoglane (3), a secondary metabolite of the marine sponge, Sarcophytum glaucum, possesses an intriguing [7.5.0.0] tricyclotetradecenone.  Its structure suggests a biogenetic cationic cascade from geranylgeranyl pyrophosphate (1) through the intermediacy of a cembrane cation (2).  The described work details efforts to construct the cembrane core (4) incorporating a halogen trigger to initiate the cyclization.  Efforts towards the synthesis of the cembrane (4) and a key synthetic intermediate, 8-trimethylsilylgeranial, will be discussed.