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

Abstract

A 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. � 2022 Wiley-VCH GmbH.