从2-甲氧基苯酚立体控制合成多官能化顺式十氢化萘：（±）-艾瑞莫佩他二酮、（±）-3β-当归酰氧基呋喃艾里莫芬烷和（±）-3β-甲基丙烯酰氧基呋喃艾里莫芬烷的全合成。
Stereocontrolled synthesis of polyfunctionalized cis-decalins from 2-methoxyphenols: total syntheses of (+/-)-eremopetasidione, (+/-)-3 beta-angeloyloxyfuranoeremophilane, and (+/-)-3 beta-methacryloyloxyfuranoeremophilane.
作者信息
Hsu Day-Shin, Hsu Po-Yi, Lee Yen-Chun, Liao Chun-Chen
机构信息
Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 300.
出版信息
J Org Chem. 2008 Apr 4;73(7):2554-63. doi: 10.1021/jo702115x. Epub 2008 Mar 7.
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, (+/-)-3 beta-angeloyloxyfuranoeremophilane, and (+/-)-3 beta-methacryloyloxyfuranoeremophilane was accomplished from creosol and ethyl vinyl ketone via a common intermediate 21.
本文描述了一种多官能化顺式十氢化萘的四步立体控制合成方法，该方法包括2-甲氧基苯酚的氧化、分子间狄尔斯-阿尔德反应、烯化反应和科普重排。通过共同中间体21，将这种有效策略应用于（±）-异瑞香素二酮、（±）-3β-当归酰氧基呋喃桉叶烷和（±）-3β-甲基丙烯酰氧基呋喃桉叶烷的全合成，原料为甲酚和乙基乙烯基酮。
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