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Review | Regular issue | Vol 83, No. 1, 2011, pp.1-46
Published online, 19th November, 2010
DOI: 10.3987/REV-10-684
Development of Samarium Diiodide-Promoted Reductive Carbon-Nitrogen Bond Cleavage Reaction of α-Amino Carbonyl Compounds: Application to the Synthesis of Biologically Active Alkaloids

Toshio Honda*

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

Abstract

Samarium diiodide (SmI2) is a mild and selective one electron transfer reagent, and has become an important tool for developing a variety of useful and unique transformations. SmI2 has been utilized in a wide range of synthetic transformations ranging from interconversion of functional groups to carbon-carbon bond forming reactions. Among the various reactions developed for SmI2, we focused our attention on its use for fragmentation reactions. We have already established a regioselective carbon-carbon bond cleavage reaction of γ-halo carbonyl compounds, and its utilization in the synthesis of various types of biologically active natural products. However, a SmI2-promoted reductive carbon-nitrogen bond cleavage reaction has received relatively little attention. In this review article, we would like to describe a general carbon-nitrogen bond cleavage reaction of α-amino carbonyl compounds and the utilization of this methodology in the synthesis of a number of bioactive alkaloids, since this reaction proceeds in relatively high yield under mild reaction conditions.