<i>Pilocarpus jaborandi</i> has been a prolific source of alkaloid natural products, including pilosinine and pilocarpine. Pilocarpine activates M3 receptors on muscle cells and is currently used as a treatment for glaucoma. Pilosinine, on the other hand, has unknown biological activity. Our interest in pilosinine is its utility as a template upon which conjugate addition methodologies can be explored. Current efforts towards the synthesis of both (+)- and (–)-pilosinine make use of conjugate addition reactions to the same nonracemic 4-phenyl-<i>N</i>-enoyl-1,3-oxazolidinone to create the lone stereocenter in each. In this way, a single stereoisomer of the chiral auxiliary results in stereodivergent outcomes, depending on the conjugate addition conditions employed. Our efforts toward the synthesis of both enantiomers of pilosinine will be presented.

Stereodivergent syntheis of (+)- and (-)-pilosinine

255th National Meeting (2018)

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