Facile Synthesis of Highly Functionalized Tricycloalkanes via Enyne Cope Rearrangement

Sarah K. Scott and Alexander J. Grenning

Department of Chemistry, University of Florida, Gainesville FL 32611-7200, USA

Terpenoid natural products and their derivatives are often targets of organic synthesis due to their promising biological activity and intriguing structural complexity. Moreover, efficient access to natural product derivatives is important for application in the drug discovery process. The work presented offers a short and simple route (four steps, three unique reactions) to access linearly fused 6/7/5 tricyclic ring systems, which represent a large class of terpenoid tricyclic natural products (dolestane, abeo-taxane, etc.). Furthermore, this work exploits the use of a rare 1,5-enyne Cope rearrangement which has previously found no application in natural product synthesis.