Total Synthesis of (-)-Steganone Utilizing a Samarium(II) Iodide Promoted 8-Endo Ketyl-Olefin Cyclization

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• 作者：Lauren G. Monovich ; Yvan Le Hué ; rou ; Magnus Rö ; nn ; and Gary A. Molander
• 刊名：Journal of the American Chemical Society
• 出版年：2000
• 出版时间：January 12, 2000
• 年：2000
• 卷：122
• 期：1
• 页码：52 - 57
• 全文大小：235K
• 年卷期：v.122,no.1(January 12, 2000)
• ISSN：1520-5126

文摘

A six-step synthesis of (±)-steganone from commercially available 3,4,5-trimethoxybenzyl alcoholfeatures 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 constructionof (-)-steganone, which exploited a chromium tricarbonyl moiety both to establish and protect the desiredabsolute stereochemistry through key transformations, including a SmI₂-promoted 8-endo radical cyclizationand two palladium-catalyzed couplings.