ChemInform Abstract: REGIO‐CONTROLLED PRENYLATION AND GERANYLATION OF 3‐FURYLMETHYLMAGNESIUM BROMIDE. SELECTIVE SYNTHESES OF 3‐SUBSTITUTED FURANOID AND 2‐SUBSTITUTED 3‐METHYLFURANOID TERPENES

DOI DOI PDF 被引用文献2件 参考文献16件 オープンアクセス
  • Araki Shuki
    Department of Synthetic Chemistry, Nagoya Institute of Technology
  • Butsugan Yasuo
    Department of Synthetic Chemistry, Nagoya Institute of Technology

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タイトル別名
  • Regio-controlled prenylation and geranylation of 3-furylmethylmagnesium bromide. Selective syntheses of 3-substituted furanoid and 2-substituted 3-methylfuranoid terpenes.

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説明

Coupling reactions of 3-furylmethylmagnesium bromide with prenyl and geranyl diethyl phosphates gave 2-substituted 3-methylfurans, rosefuran and sesquirosefuran, as the main products. When the reactions were carried out in the presence of a catalytic amount of copper(I) iodide, normal coupling occurred and 3-substituted furans, perillene and dendrolasin, were formed in good yields. The related naturally occurring 3-substituted thiophene, 3-(4-methyl-3-pentenyl)thiophene, was also synthesized from 3-thienylmethylmagnesium bromide and prenyl diethy phosphate.

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