Efficient strategy for the stereoselective synthesis of 2,3-disubstituted benzo[α]quinolizidine alkaloids: concise synthesis of (−)-protoemetinol
2015
Moon, Hyunyoung | An, Hongchan | Sim, Jaehoon | Kim, Kyeojin | Paek, Seung-Mann | Suh, Young-Ger
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.
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