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Review | Regular issue | Vol 81, No. 12, 2010, pp.2719-2747
Published online, 17th November, 2010
DOI: 10.3987/REV-10-683
Development of Samarium Diiodide-Promoted Regioselective Carbon-Carbon Bond Cleavage Reaction of γ-Halo- and ε-Halo-α,β-unsaturated Carbonyl Compounds: Application to the Synthesis of Biologically Active Natural Products

Toshio Honda*

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


Samarium diiodide (SmI2), a mild and selective one electron transfer reagent, has been utilized in a wide range of synthetic transformations. Among the various reactions developed for SmI2, we focused on its use for fragmentation reactions, and established a regioselective carbon-carbon bond cleavage reaction of γ-halo carbonyl compounds. Utilization of this strategy in the synthesis of various types of biologically active natural products is discussed in this review article.