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Pure Appl. Chem., 2008, Vol. 80, No. 4, pp. 717-726

Heterocycle synthesis via radical reactions

Takeaki Naito

Medicinal Chemistry Laboratory, Kobe Pharmaceutical University 4-19-1, Motoyamakita, Higashinada, Kobe 658-8558, Japan

Abstract: A novel synthetic method for the preparation of nitrogen-containing heterocycles via the route involving domino-type radical addition/cyclization reaction of oxime ethers is described. Alkyl radical addition/cyclization of oxime ethers carrying an appropriate leaving group proceeded smoothly to form the alkylated nitrogen-containing heterocyclic compounds. Additionally, tin-mediated radical addition/cyclization/elimination (RACE) reaction of oxime ethers is newly found and successfully applied to an asymmetric total synthesis of (-)-martinellic acid.