Stereospecific annulation and sequential ring-opening of (R)-carvone: Formation of a novel tricyclic dione

Article abstract of DOI:10.1016/S0040-4039(00)77053-5

Free radical annulation followed by trimethylsilyl iodide-promoted ring- opening of (R)-carvone-dichloroketene adducts leads to an unusual carbon skeleton rearrangement. The carbonyl group of carvone enhances the reactivity of the radical cyclization, changes the ring-opening pathway and leads to the formation of a new tricyclic dione product.