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.

In the presence of iodine, a functional group compatible method for the deprotection of tert-butanesulfinyl and p-toluenesulfinyl units was developed.

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Natural products with oxa-bridged medium-sized carbocyclic ring structure units play an important role in nature. Therefore, developing novel and efficient methods is essential for synthesizing complex natural products containing oxygen-bridged rings. In this article, pro-gress toward the synthesis of oxygen-bridged seven and eight-membered rings is reviewed in terms of the strategies employed.