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Paper | Special issue | Vol 79, No. 1, 2009, pp.521-529
Published online, 22nd September, 2008
DOI: 10.3987/COM-08-S(D)12
De Novo Asymmetric Approach To 8a-epi-swainsonine

Jason A. Coral, Haibing Guo, Mingde Shan, and George A. O’Doherty*

*Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA


An improved method for the synthesis of (-)-8a-epi-swainsonine has been developed with 9 fewer steps than the original route. The synthetic improvements include a two-step procedure for the preparation of benzyl 4-(furan-2-yl)-4-oxobutylcarbamate from pyrrolidin-2-one and a two-step procedure for the preparation of benzyl 3-((3aS,4S,6R,7aR)-4-(benzyloxy)tetrahydro-2,2-dimethyl-7-oxo-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)- propylcarbamate from benzyl 3-((2R,6S)-6-(benzyloxy)-3,6-dihydro-3-oxo-2H-pyran-2- yl)propylcarbamate.