Samarium Diiodide Mediated Reactions in Total Synthesis

Authors

  • K. C. Nicolaou Prof. Dr.,

    1. Department of Chemistry
    2. The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA), Fax: (+1) 858-784-2469
    3. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • Shelby P. Ellery,

    1. Department of Chemistry
    2. The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA), Fax: (+1) 858-784-2469
    3. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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  • Jason S. Chen Dr.

    1. Department of Chemistry
    2. The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA), Fax: (+1) 858-784-2469
    3. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA)
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Abstract

Introduced by Henri Kagan more than three decades ago, samarium diiodide (SmI2) has found increasing application in chemical synthesis. This single-electron reducing agent has been particularly useful in C[BOND]C bond formations, including those found in total synthesis endeavors. This Review highlights selected applications of SmI2 in total synthesis, with special emphasis on novel transformations and mechanistic considerations. The examples discussed are both illustrative of the power of this reagent in the construction of complex molecules and inspirational for the design of synthetic strategies toward such targets, both natural and designed.

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