Regiocontrolled formation of 4,5-dihydro-3(2H)-furanones from 2-butyne-1,4-diol derivatives. Synthesis of bullatenone and geiparvarin.
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概要
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Two new methods for selective hydration of 1,1,4-trisubstituted 2-butyne-1,4-diols (<B>1</B>) to give 4,5-dihydro-3(2<I>H</I>)-furanone derivatives are reported. The first involves selective monoacetylation of the less hindered hydroxyl group of <B>1</B> followed by Ag(I)-catalyzed rearrangement and cyclization to give 3-acetoxy-2,2,5-trisubstituted 2,5-dihydrofurans (<B>2</B>). Final hydrolysis yielded 2,2,5-trisubstituted 4,5-dihydro-3(2<I>H</I>)-furanones. Oxidation of the enol acetates <B>2</B> with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone gave 3(2<I>H</I>)-furanones. The new method was applied to the synthesis of naturally occurring 3(2<I>H</I>)-furanones such as bullatenone and geiparvarin from the corresponding 2-butyne-1,4-diol derivatives. The second approach is concerned with the synthesis of the opposite regioisomer, 2,5,5-trisubstituted 4,5-dihydro-3(2<I>H</I>)-furanones, from diols <B>1</B> with a polymer reagent Hg/Nafion-H.
- 公益社団法人 日本化学会の論文
著者
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Saimoto Hiroyuki
Department Of Chemistry And Biotechnology Graduate School Of Engineering Tottori University
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Nozaki Hitosi
Department of Industrial Chemistry, Faculty of Engineering Kyoto University
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Hiyama Tamejiro
Department of Industrial Chemistry, Faculty of Engineering, Kyoto University
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