Polycylic structures are found in nearly every biosynthetic class of natural products. In particular, an amazing range of rigid densely functionalized polycylic compounds are formed from simple polyisoprenoid precursors during terpene biosynthesis. Examples include Taxol (a widely used anticancer drug) and the ginkgolides (active ingredients in Ginkgo biloba). Related strategies are used in alkaloid biosynthesis, leading to complex polycyclic products with nitrogen functionalities.
We are developing a diversity-oriented synthesis in which multiple polycyclic scaffolds are synthesized from a small set of relatively simple starting materials. A variety of cyclization reactions are then used to generate diverse polycyclic molecules related to alkaloid and terpenoid natural products.
