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Paper | Special issue | Vol 67, No. 1, 2006, pp.189-204
Published online, 5th July, 2005
DOI: 10.3987/COM-05-S(T)12
Chiral Synthesis of (+)-Febrifugine and (-)-Isofebrifugine by Means of Samarium Diiodide-promoted Carbon-Nitrogen Bond Cleavage Reaction

Miho Katoh, Ryuichiro Matsune, and Toshio Honda*

*Institute of Medical Chemistry, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

(+)-Febrifugine, a potential anti-malarial piperidine alkaloid, was synthesized from (4S)-hydroxyproline methyl ester, stereoselectively, where a samarium diiodide-promoted carbon-nitrogen bond cleavage reaction was involved as a key reaction. A stereocontrolled formal synthesis of (-)-isofebrifugine was also described.