Nature-Inspired Stereospecific Total Synthesis of P-(+)-Dispegatrine and Four Other Monomeric Sarpagine Indole Alkaloids


  • We wish to acknowledge the NIMH (in part) and the Lynde and Harry Bradley Foundation for support of this work. X-ray crystallographic studies were carried out at the Naval Research Laboratory and supported by NIDA-NRL Interagency Agreement Number Y1-DA1101.


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All five: The first total synthesis of the C2-symmetric indole alkaloid 1 involved a late-stage thallium(III) acetate-mediated intermolecular oxidative coupling to construct the C9[BOND]C9′ bond with complete regio- and stereocontrol. The formation of a single atropodiastereomer in this critical step arises from internal asymmetric induction. The first total synthesis of four other monomeric sarpagine indole alkaloids is also described.