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Paper | Special issue | Vol 69, No. 1, 2006, pp.193-216
Published online, 23rd May, 2006
DOI: 10.3987/COM-06-S(O)9
Novel Chiral Synthetic Path to Indolizidine and Quinolizidine Alkaloids by Means of a Samarium Diiodide-Promoted Reductive Carbon-Nitrogen Cleavage Reaction: Synthesis of (+)-(8R, 8aR)-Perhydro-8-indolizidinol and (—)-Deoxynupharidine

Miho Katoh, Hirotake Mizutani, and Toshio Honda*

*Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Novel chiral synthetic procedures for indolizidine and quinolizidine alkaloids were developed, where a samarium diiodide-promoted carbon-nitrogen bond cleavage reaction was employed as a key step. Application of the procedure led to the total synthesis of (+)-(8R, 8aR)-perhydro-8-indolizidinol and (-)-deoxynupharidine.