Simple and efficient synthesis of bicyclic enol-carbamates: access to brabantamides and their analogues

Abstract

A novel synthetic approach towards the formation of the unusual bicyclic enol-carbamates, as found in brabantamides A-C, is reported. The bicyclic oxazolidinone framework was obtained in very good yield and with high E/Z selectivity from a readily available β-ketoester under mild reaction conditions using Tf₂O and 2-chloropyridine tandem. The major E isomer was used in the synthesis of the brabantamide A analogue.