Total Synthesis of (−)‐Magnoshinin and (+)‐Merrilliaquinone: Application of a Late‐Stage Oxidative Functionalization Protocol

Abstract

AbstractA unified approach for the first enantioselective total synthesis of magnoshinin and merrilliaquinone is reported. The key feature of the synthesis is the DDQ assisted chemoselective late‐stage oxidative functionalization of the polyoxygenated chiral tetralin core accessed by utilizing the relayed asymmetric induction strategy. Then, the follow‐up of chemoselective redox chemistry facilitates the synthesis of (−)‐magnoshinin (28.2 % overall yield) and (+)‐merrilliaquinone (20.6 % overall yield) along the shortest route, starting from the known 3‐(2,4,5‐trimethoxyphenyl)propanoic acid.