A novel asymmetric aza-Prins and aza-silyl Prins cyclizations has been developed for the first time, providing straight forward access to substituted piperidines with excellent enantioselectivity. It is possible to introduce a range of different substituents into the heterocycles through a choice of Lewis/Bronsted acid and solvent(s), with halo-, phenyl-, hydroxy-, keto and amido-substituted piperidine products all being accessed through these highly enantioselective processes.<br/><br/>This research methodology aims to produce a short route for the enantioselective total synthesis of piperidine and aza sugar natural products. The natural products such as Dendrobate alkaloid (+)-epi-241D, (-)-solenopsin A, (+)-epi-dihydropinidine and swainsonine would be excellent targets to showcase this novel methodology in total synthesis and hence reduce the number of steps in the overall synthesis of these important synthetic targets.

Asymmetric aza-Prins reaction: Application to the total synthesis of dendrobate alkaloid (+)-epi-241D, (-)-solenopsin A, (+)-epi-dihydropinidine and swainsonine

256th National Meeting (2018)

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