Cyclooctane rings are found in numerous classes of biologically active natural products. Yet their construction remains a constant challenge. Current methods to form cyclooctane systems often suffer from a lack of selectivity resulting in the formation of product mixtures. The development and proposed asymmetric synthesis toward a common core structure seen in many classes of natural products is described. Our proposed method allows the rapid construction of a heterocyclic [3.3.1] bicycle. The key step utilizing a transition metal catalyzed isomerization.

Progress towards the synthesis of eight-membered heterocyclic natural products

251st National Meeting (2016)

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