title: Formyl Group Activation of a Bromopyrrole Ester in Suzuki Cross-Coupling Reactions: Application to a Formal Synthesis of Polycitone A and B and Polycitrin A.
abstract: A new pyrrole building block is described, which allows for the regiospecific synthesis of 2,3,5-trisubstituted pyrroles and 2,3,4,5- tetrasubstituted pyrroles. Optimization studies are presented for the preparation of the pyrrole building block along with the evaluation of various cross-coupling conditions and cross-coupling agents. A short, formal synthesis of the natural products Polycitone A, Polycitone B and Polycitrin A from the pyrrole building block is also described.
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: John T
authors.initials: JT
authors.lastname: Gupton
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: Nakul
authors.initials: N
authors.lastname: Telang
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: Michael
authors.initials: M
authors.lastname: Wormald
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: Kristin
authors.initials: K
authors.lastname: Lescalleet
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: Jon
authors.initials: J
authors.lastname: Patteson
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: Will
authors.initials: W
authors.lastname: Curry
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: Andrew
authors.initials: A
authors.lastname: Harrison
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: Megan
authors.initials: M
authors.lastname: Hoerrner
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: John
authors.initials: J
authors.lastname: Sobieski
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: Michael
authors.initials: M
authors.lastname: Kimmel
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: Emily
authors.initials: E
authors.lastname: Kluball
authors.affiliation: Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
authors.forename: Thomas
authors.initials: T
authors.lastname: Perry
keywords: Marine Natural Products; Pyrrole; Suzuki Cross-Coupling; Vilsmeier Formylation