title: Studies on the regio- and diastereo-selective epoxidation of daphnanes and tiglianes.
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.
authors.affiliation: Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305-5080, USA.
authors.forename: Pierre-Luc
authors.initials: PL
authors.lastname: Boudreault
authors.affiliation: Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305-5080, USA.
authors.forename: Jennifer K
authors.initials: JK
authors.lastname: Mattler
authors.affiliation: Department of Chemistry, Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305-5080, USA.
authors.forename: Paul A
authors.initials: PA
authors.lastname: Wender
keywords: Daphnane; Epoxidation; Protein kinase C; Tigliane