Abstract
AbstractThis thesis consists of two parts : the first part is concerned with diastereoselective intermolecular Diels-Alder reactions of masked o-benzoquinones (MOBs) with homochiral acrylates. The second part describes the applications of MOBs toward the total synthesis of (+)-Drechslerine D and (+)-Drechslerine E.In chapter 1, the asymmetric Diels-Alder reactions of various MOBs with homochiral acrylate 70 and methacrylate 71, affording high chemo-, regio- and stereo-selectivities.In chapter 2, the bicyclo[3.2.1]octanone 169 was obtained intermolecular Diels-Alder reaction, photochemical oxa-di-□-methane rearrangement, and regioselective ring opening of the strained cyclopropane ring in three steps. Starting from vanilline 173, the bicyclo [3.2.1]octanone skelton was constructed in nine steps. Compound 191 was employed as the model system study, Claisen rearrangement, Wacker reaction and Baeyer-Villiger oxidation were applied sequentially to afford compound 200. Finally, we hope to accomplish the total synthesis of (+)-drechslerine D and (+)-drechslerine E within several steps in the future.