Studies on the regio- and diastereo-selective epoxidation of daphnanes and tiglianes

Pierre-Luc Boudreault; Jennifer K Mattler; Paul A Wender

doi:10.1016/j.tetlet.2015.01.126

Studies on the regio- and diastereo-selective epoxidation of daphnanes and tiglianes

Tetrahedron Lett. 2015 Jun;56(23):3423-3427. doi: 10.1016/j.tetlet.2015.01.126.

Authors

Pierre-Luc Boudreault¹, Jennifer K Mattler¹, Paul A Wender¹

Affiliation

¹ Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305-5080, USA.

Abstract

Daphnanes and tiglianes are diterpenes with a shared tricyclic 5-7-6 ring system. Many members exhibit significant biological activities often associated with protein kinase C signaling. Many of these natural products (~100) have a C6-C7 α-epoxide whose influence on biological activity is little studied. Using the more readily available phorbol ester PDBu as a test substrate, we report an efficient, and potentially general, α-epoxidation method based on a vanadium-catalyzed asymmetric epoxidation with bishydroxamic acid (BHA) ligands.

Keywords: Daphnane; Epoxidation; Protein kinase C; Tigliane.

Abstract

Grants and funding