1,3-diol fragmentation using a reactive benzylic hydroxyl group as a nucleofuge. Synthesis of a tobacco sesquiterpene.

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概要

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• A benzylic hydroxyl group activated by electron-donative aromatic function was found to be a remarkably reactive nucleofuge for 1,3-diol fragmentation. Thus, treatment of α-(2,6-dimethoxy-4-methylphenyl)-2β-hydroxy-2α,5,5,8aβ-tetramethyl-4aα-decahydro-lβ-naphthalenemethanol with pyridinium chloride or pyridinium <I>p</I>-toluenesulfonate in dichloromethane underwent the 1,3-diol fragmentation smoothly to produce <I>r</I>-1-[(<I>E</I>)-2-(2,6-dimethoxy-4-methylphenyl)ethenyl]-<I>t</I>-2-(3-oxobutyl)-1,3,3-trimethylcyclohexane (<B>24</B>) in quantitative yield. Starting from <B>24</B>, a tobacco sesquiterpene, 4-(2,2,6-trimethyl-6-vinylcyclohexyl)-2-butanone, was synthesized in racemic form by seven steps.

• 公益社団法人 日本化学会の論文

著者

• Yoshikoshi Akira

  Chemical Research Institute Of Non-aqueous Solutions Tohoku University

• Kato Michiharu

  Chemical Research Institute of Non-Aqueous Solutions, Tohoku University

• Tooyama Youichi

  Chemical Research Institute of Non-Aqueous Solutions, Tohoku University

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• 1,3-diol fragmentation using a reactive benzylic hydroxyl group as a nucleofuge. Synthesis of a tobacco sesquiterpene.
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