A concise total synthesis of (±)-mesembrine has been successfully accomplished in seven steps and 24% overall yield from commercially available 3-ethoxy-2-cyclohexen-1-one. Central to the assembly of the skeleton of mesembrine are a Johnson-Claisen rearrangement for the formation of the benzylic quaternary stereocenter and direct allylic oxidation to generate the substrate for the amidation/transannular aza-conjugate addition reaction.
This work was supported by the Basic Science Research Program from the National Research Foundation of Korea (NRF-2016R1C1B1008816) funded by the Ministry of Education and the 2017 Research Fund of the Catholic University of Korea.Noaitnal Reseacrh Foundoaitn of Koera N(RF-2016R1C1B1008816)