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

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posted on 2008-04-04, 00:00 authored by Day-Shin Hsu, Po-Yi Hsu, Yen-Chun Lee, Chun-Chen Liao
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, (±)-3β-angeloyloxyfuranoeremophilane, and (±)-3β-methacryloyloxyfuranoeremophilane was accomplished from creosol and ethyl vinyl ketone via a common intermediate 21.

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