Enantioselective Total Synthesis of (+)-Homochelidonine by a PdII-Catalyzed Asymmetric Ring-Opening Reaction of a meso-Azabicyclic Alkene with an Aryl Boronic Acid

Authors

  • Helen A. McManus Dr.,

    1. Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George St., Toronto, ON M5S 3H6, Canada, Fax: (+1) 416-946-8185
    Search for more papers by this author
  • Matthew J. Fleming Dr.,

    1. Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George St., Toronto, ON M5S 3H6, Canada, Fax: (+1) 416-946-8185
    Search for more papers by this author
  • Mark Lautens Prof.

    1. Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George St., Toronto, ON M5S 3H6, Canada, Fax: (+1) 416-946-8185
    Search for more papers by this author

  • We thank the NSERC, Merck Frosst Canada, and the University of Toronto for support of our programs, Jérémy Ruiz for initial studies using the N-Cbz azabicycle, Alena Rudolph for initial studies into the enantioselective reaction, and Dr. Christopher Dockendorff for first bringing this natural product to our attention.

Abstract

original image

Eine effiziente und hochkonvergente enantioselektive Synthese von (+)-Homochelidonin (siehe Schema; Cbz=Benzyloxycarbonyl, MOM=Methoxymethyl) beruht auf einer neuen und leistungsfähigen desymmetrisierenden Ringöffnung eines meso-Azabicyclus mit einer Arylboronsäure, die auch andere Hexahydrobenzo[c]phenanthridin-Alkaloide zugänglich machen sollte.

Ancillary