Pilosinine and pilocarpine, naturally occurring alkaloids produced by a member of the Pilocarpus jaborandi, have received substantial attention as compounds which act as partial agonists of the muscarine-M3 receptors. Our recent efforts have demonstrated opposite stereochemical outcomes when utilizing allylic organocopper and organostannane nucleophiles in asymmetric conjugate addition reactions to nonracemic 4-phenyl-N-enoyl-1,3-oxazolidinones. Through the application of these results, a single enantiomer of this common chiral auxiliary can effectively enable the synthesis of (+)- and (�)-pilosinine, along with (+)-pilocarpine and isopilocarpine. Our progress toward utilizing this flexible strategy will be highlighted as providing ample opportunity for preparation of potentially important analogs of the parent compounds.

Stereodivergent conjugate addition reactions for synthesis of pilocarpine and pilosinine

245th National Meeting (2013)

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