Synthesis of Oxa-Bridged Medium-Sized Carbocyclic Rings via Prins Cyclization.

Herein, we report a new method for the synthesis of oxa-bridged carbocyclic units based on intramolecular Prins reaction of dioxinones. Our new synthetic approach is flexible and practical and has been successfully applied to the preparation of highly functionalized seven-, eight-, and nine-membered carbocycles. The potential utility of this approach has also been demonstrated in a model study toward construction of the 7,8-fused ring system presented in neoabyssomicin D.