Convergent Total Synthesis of Lamellarins and Their Congeners

J Org Chem. 2020 Jul 2;85(13):8603-8617. doi: 10.1021/acs.joc.0c00998. Epub 2020 Jun 18.

Abstract

A convergent total synthesis of lamellarins S and Z is described. The synthesis features a halogen dance of an easily accessible α,β-dibromopyrrole promoted by an ester moiety. The resultant β,β'-dibromopyrrole undergoes a ligand-controlled Suzuki-Miyaura coupling to provide a range of diarylated pyrrole derivatives. The established synthetic method was also applicable to the synthesis of ningalin B and lukianols A and B.

Publication types

  • Research Support, Non-U.S. Gov't