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

John T Gupton; Nakul Telang; Michael Wormald; Kristin Lescalleet; Jon Patteson; Will Curry; Andrew Harrison; Megan Hoerrner; John Sobieski; Michael Kimmel; Emily Kluball; Thomas Perry

doi:10.1016/j.tet.2014.02.091

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

Tetrahedron. 2014 Apr 1;70(17):2738-2745. doi: 10.1016/j.tet.2014.02.091.

Affiliation

¹ Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.

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.

Keywords: Marine Natural Products; Pyrrole; Suzuki Cross-Coupling; Vilsmeier Formylation.

Grants and funding

R15 CA067236/CA/NCI NIH HHS/United States