Stereocontrolled Synthesis of Polyfunctionalized cis-Decalins from 2-Methoxyphenols: Total Syntheses of (()-Eremopetasidione, (()-3â-Angeloyloxyfuranoeremophilane, and (()-3â-Methacryloyloxyfuranoeremophilane

نویسندگان

  • Day-Shin Hsu
  • Po-Yi Hsu
  • Yen-Chun Lee
  • Chun-Chen Liao
چکیده

A four-step stereocontrolled synthesis of polyfunctionalized cis-decalins is described, involving oxidation of 2-methoxyphenol, intermolecular Diels-Alder reaction, olefination, and Cope rearrangement. Application of this efficient strategy to the total syntheses of (()-eremopetasidione, (()-3â-angeloyloxyfuranoeremophilane, and (()-3â-methacryloyloxyfuranoeremophilane was accomplished from creosol and ethyl vinyl ketone via a common intermediate 21.

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تاریخ انتشار 2008