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.