Pure Appl. Chem., 2008, Vol. 80, No. 4, pp. 717-726
doi:10.1351/pac200880040717
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.
Keywords: domino reaction: bgugaine; martinellic acid; oxime ethers; radical reaction.
*Paper based on a presentation at the 21st International Congress for Heterocyclic Chemistry (ICHC 21), 15-20 July 2007, Sydney, Australia. Other presentations are published in this issue, pp. 669-805.