Total Synthesis of (−)-Steganone Utilizing a Samarium(II) Iodide Promoted 8-Endo Ketyl−Olefin Cyclization
Journal of the American Chemical Society1999Vol. 122(1), pp. 52–57
Citations Over TimeTop 15% of 1999 papers
Abstract
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.
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