汎用的かつ立体選択的な三置換オレフィン構築法の開発とそれを用いたプラウノトールの効率的全合成

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  • Practical and Effective Total Synthesis of Plaunotol via Novel and Stereoselective Method for Construction of Tri-substituted Olefins.
  • ハンヨウテキ カツ リッタイ センタクテキ ナ 3 チカン オレフィン コウチクホウ ノ カイハツ ト ソレ オ モチイタ プラウノトール ノ コウリツテキ ゼンゴウセイ

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Plaunotol, a known antiulcer drug, has antibacterial activities against Hericobacter pylori. We developed the efficient and practical synthesis of plaunotol and its derivatives. In order to construct C6-C7 tri-substituted allylic alcohol with high stereoselectivity, the Homer-Wadsworth-Emmons reaction with novel reagent and the Wittig reaction with α-acetalketones were developed. These methods were found to give a range of tri-substituted olefin moieties. Using (E)-α-bromoacrylate as a key intermediate, which was prepared from novel reagent-methyl bis (2, 2, 2-trifluoroethoxy) bromophosphonoacetate, the most effective route of plaunotol synthesis via Suzuki cross-coupling was achieved. Moreover the most practical synthesis of plaunotol was achieved via Z-selective Wittig reaction using α-acetalketone. In search for high antibacterial activities, we designed plaunotol thiourea derivatives and diol derivatives. These derivatives were synthesized regioselectively using our effective synthetic route to plaunotol. Their antibacterial activities against Hericobactor pylori are described and the C1-phenethylthiourea derivative was the most potent antibacterial agent.

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