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Paper | Regular issue | Vol 68, No. 12, 2006, pp.2587-2594
Published online, 17th October, 2006
DOI: 10.3987/COM-06-10887
Total Synthesis of (±)-2-epi-Validamine

Hiroaki Okamura,* Hiroshi Nagaike, Nsiama Tienabe Kipassa, Tetsuo Iwagawa, and Munehiro Nakatani

*Department of Chemistry and Bioscience, Faculty of Science, Kagoshima University, 1-21-35 Korimoto, Kagoshima 890-0065, Japan

Abstract

(±)-Validamine and its epimers, (±)-2-epi-validamine (DL-5a-carba-α-mannopyranosylamine) and (±)-2-epi-3-epi-validamine (DL-5a-carba-α-altropyranosylamine) were synthesized from a poly-functionalized bicyclolactam that obtained by a base-catalyzed Diels-Alder reaction of N-tosyl-3-hydroxy-2-pyridone and methyl acrylate. All isomers were prepared via a common key intermediate in six or seven steps.