A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE

Abstract

We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkaloid DHβE. Preliminary pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings.

Keywords

• DhβE
• Mizoroki–Heck cross-coupling reaction
• 6π-electrocyclization
• [6,6]-bicyclic lactone
• vinyl halide