Construction of the A-B-C Ring of Simplicissin through an Oxidative Dearomatization/Iodination/[3+2] Annulation Cascade.

As an attractive DMOA-derived spiromeroterpenoid, simplicissin shares a common A-B-C ring skeleton with other natural analogues. On the basis of the development of an oxidative dearomatization/iodination/[3+2] annulation cascade, a concise synthetic pathway to the A-B-C ring of simplicissin has been successfully established, and the substrate generality of the novel oxidative dearomatization/iodination/[3+2] annulation cascade has been checked.