Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization

Org Lett. 2021 Sep 17;23(18):7285-7289. doi: 10.1021/acs.orglett.1c02767. Epub 2021 Aug 30.

Abstract

The first total synthesis of the natural product impatien A is described. This concise synthesis features an aza-Heck cyclization to construct the complex spirocyclic ring system and provides a rare example of the use of aza-Heck cyclizations in complex molecule synthesis. To enable this key cyclization of an electrophilic nitrogen atom with a tetrasubstituted alkene, we utilized high-throughput experimentation to identify a new ligand and ultimately deliver impatien A in seven steps from known compounds.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Biological Products
  • Cyclization
  • Impatiens / chemistry*
  • Ligands
  • Molecular Structure
  • Nitrogen / chemistry*
  • Stereoisomerism

Substances

  • Biological Products
  • Ligands
  • Nitrogen