Enantioselective cyclization of enamide-ynes and application to the synthesis of the kopsifoline core

Britton K Corkey; Stephen T Heller; Yi-Ming Wang; F Dean Toste

doi:10.1016/j.tet.2013.02.091

Enantioselective cyclization of enamide-ynes and application to the synthesis of the kopsifoline core

Tetrahedron. 2013 Jul 8;69(27-28):5640-5646. doi: 10.1016/j.tet.2013.02.091.

Authors

Britton K Corkey¹, Stephen T Heller, Yi-Ming Wang, F Dean Toste

Affiliation

¹ Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, USA.

Abstract

We report the palladium-catalyzed enantioselective cyclization of 1,6-enamidynes to form spirocyclic ring systems. We applied this methodology to the concise synthesis of the skeletal core of the kopsifoline alkaloids.

Keywords: Palladium catalysis; electrophilic activation; enantioselective synthesis; natural product synthesis; spirocyclization.

Grants and funding

R01 GM073932/GM/NIGMS NIH HHS/United States