65 新しい酸化剤系CrO_3-HBF_4-CH_3CNを用いたネオリグナン類の生合成を模した合成研究

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概要

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• Oxidation of several phenylpropenes by a new oxidizing reagent system CrO_3-HBF_4-CH_3CN which was founded after the theory of solvent effects, gave the interesting C-C coupling products which have ketone group in benzyl position. These results provide a useful synthetic method for the potential biological active lignans and neo-lignans. 1. Preliminary investigations and syntheses of aryltetrahydro-phthalide lignans (7), (11) and tetrahydrofuran lignans (9), (13) Oxidation of phenylpropenes (5) and (8) by the new reagent system gave the tetralone (6) and (10) and tetrahydrofuran lignan (9), and the tetralone (6) and (10) were transformed to the (7) and (11), subsequently. In comparison, oxidation of (5) by [Fe(bpy)_3](ClO_4)_3afforded a phthalide (12) and a tetrahydrofuran (13a) or (13b). 2. Synthesis of dibenzocyclooctadiene lignan Oxidation of the biphenylpropene (16) by the new reagent gave a cyclooctatrienone (22) but (19) and (21) did not afforded any cyclized products. 3. Synthesis of podophyllotoxone Oxidation of the ester (24) by the same reagent gave the lactone (25), (26) and isopodophyllotoxone (27).

• 天然有機化合物討論会の論文
• 1981-09-10

著者

• 小谷 栄一

  Showa College of Pharmaceutical Sciences

• 飛永 精照

  昭和薬大

• 小谷 栄一

  昭和薬大

• 小谷 榮一

  昭和薬科大学

• 飛永 精照

  昭和薬科大学

• 竹谷 哲也

  昭和薬科大学

• 竹谷 哲也

  昭和薬大

• 小谷 栄一

  昭和薬科大学

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