Efficient strategy for the stereoselective synthesis of 2, 3-disubstituted benzo[α]quinolizidine alkaloids: concise synthesis of (−)-protoemetinol. Issue 4 (21st January 2015)

• Record Type: Journal Article
• Authors: Moon, Hyunyoung; An, Hongchan; Sim, Jaehoon; Kim, Kyeojin; Paek, Seung-Mann; Suh, Young-Ger
• Is Part Of: Tetrahedron letters. Volume 56:Issue 4(2015)
• Page Start: 608
• Page End: 611
• Publication Date: 2015-01-21
• Subjects: (−)-Protoemetinol -- Benzo[α]quinolizidine alkaloid -- Cross metathesis -- Aza-Claisen rearrangement -- Transannulation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2014.12.030
• Languages: English
• ISSNs: 0040-4039

Abstract

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.