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Asymmetric Total Synthesis of Arcutinidine and Arcutinine
preprintsubmitted on 30.05.2019, 03:49 and posted on 30.05.2019, 15:37 by Shupeng Zhou, Kaifu Xia, Ang Li
We have accomplished the asymmetric total synthesis of arcutinidine and arcutinine, two arcutine-type C20-diterpenoid alkaloids. A pentacyclic intermediate was rapidly assembled by using two Diels−Alder reactions. A cascade sequence of Prins cyclization and Wagner−Meerwein rearrangement was then developed to construct the core of arcutinidine, which was further elaborated into an oxygenated pentacycle through a scalable route. Chemoselective reductive amination followed by spontaneous imine formation furnished the pyrroline motif at a final stage.