- Total Synthesis of (-)-Steganone Utilizing a Samarium(II) Iodide Promoted 8-Endo Ketyl-Olefin Cyclization
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A six-step synthesis of (±)-steganone from commercially available 3,4,5-trimethoxybenzyl alcohol features a samarium(II) iodide promoted 8-endo ketyl-olefin coupling to install, in a single transformation, the 8,5 ring system common to the lignan lactones. The racemic synthesis provided the basis for the construction of (-)-steganone, which exploited a chromium tricarbonyl moiety both to establish and protect the desired absolute stereochemistry through key transformations, including a SmI2-promoted 8-endo radical cyclization and two palladium-catalyzed couplings.
- Monovich, Lauren G.,Le Huerou, Yvan,Roenn, Magnus,Molander, Gary A.
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