非天然型キニーネの実用的全合成を目指して

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タイトル別名
  • Development of Highly Efficient Organocatalytic Reaction toward Practical Total Synthesis of ent-Quinine
  • ヒテンネンガタ キニーネ ノ ジツヨウテキ ゼン ゴウセイ オ メザシテ

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<p>Recently, cinchona alkaloids such as quinine and quinidine were re-focused as next generation organocatalysts. Therefore, practical total syntheses of enantiomers of these alkaloids are required in current chemical society. Thus, efficient protocol for preparation of C4-alkyl substituted chiral piperidines using secondary amine catalyzed formal aza[3+3]cycloaddition reaction using aliphatic α,β-unsaturated aldehydes and thiomalonamate derivatives were discovered as key step in total synthesis. In our reaction system, thiomalonamate is excellent nucleophile, and the addition of suitable acid and it’s amounts are important factor for the acceleration effect in organocatalytic reaction. These efforts lead to only 0.1 mol% catalyst loading in multi-gram scale synthesis for suitable reaction time.</p>

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