Formal Alder-ene reaction of a bicyclo[1.1.0]butane in the synthesis of the tricyclic quaternary ammonium core of daphniglaucins.
A tricyclic substructure of the tetracyclic nitrogen core of the daphniglaucins was formed by an oxidative activation of the allyl side chain of a bicyclo[1.1.0]butylmethylamine, a spontaneous intramolecular formal Alder-ene reaction, and a selective cyclization of a triol intermediate.
Ueda
Masafumi
M
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Walczak
Maciej A A
MA
Wipf
Peter
P