Efficient generation of ortho-quinone methide: application to the biomimetic syntheses of (±)-schefflone and tocopherol trimers.

An efficient method using silver oxide-mediated oxidation for the synthesis of ortho-quinone methides has been developed and applied to the biomimetic syntheses of novel trimeric natural products, (±)-schefflone and tocopherol trimers. Further studies of the critical trimerization as well as substrate scope and limitations are also reported.