Samarium Diiodide Mediated Reactions in Total Synthesis

Introduced by Henri Kagan more than three decades ago, samarium diiodide (SmI(2)) has found increasing application in chemical synthesis. This single-electron reducing agent has been particularly useful in C-C bond formations, including those found in total synthesis endeavors. This Review highlights selected applications of SmI(2) 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.