Efficient strategy for the stereoselective synthesis of 2, 3-disubstituted benzo[α]quinolizidine alkaloids: concise synthesis of (−)-protoemetinol. Issue 4 (21st January 2015) - Moon, Hyunyoung
Graphical abstract: Abstract: The stereoselective synthesis of (−)-protoemetinol has been accomplished through nine steps from a known homoallylic amine. The key steps of the synthesis involve the efficient preparation of an aza-Claisen rearrangement (ACR) precursor using cross metathesis and amide enolate-induced ACR followed by acid-catalyzed transannulation for the elaboration of the benzo[α]quinolizine skeleton and three stereogenic centers. This unique synthetic route envisages a unified and versatile strategy for the synthesis of 2, 3-disubstituted benzo[α]quinolizidine.