Reactivity of Isocoumarins. I. Effect of a Neighboring Hydroxyl Group on the Reduction of the Lactone Carbonyl Group

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概要

• 論文の詳細を見る

• The reduction of 3,4-dihydroisocoumarins (1,3,6,11a, 11b, and 12b) having a hydroxyl group or acetoxyl group at the C_<(8)>-position adjacent to the lactone carbonyl group with lithium aluminum hydride gave novel products, 1,8-dihydroxyisochromans (10a, 13,and 16a), in addition to 8-hydroxyisochromans (2,8,and 14) and 2-(3-hydroxy-2-hydroxymethylphenyl)-ethanols (4,9,and 15). The isochromans and 2-(2-hydroxymethylphenyl)-ethanols are known reduction products of 3,4-dihydroisocoumarins lacking a C_<(8)>-hydroxyl group. In addition, 13 was obtained selectively in 50% yield by reduction of the magnesium chelate of 11a with lithium aluminum hydride. Similarly, 8-hydroxy-3-phenylisocoumarin (23a) and 8-acetoxy-3-phenylisocoumarin (23b) both gave 2-formyl-3-hydroxybenzyl phenyl ketone (24). Based on these results, a mechanism for the reduction of 8-hydroxy-3,4-dihydroisocoumarins is proposed, as shown in Chart 3.

• 公益社団法人日本薬学会の論文
• 1980-03-25

著者

• 小山 鷹二

  Faculty of Pharmaceutical Sciences, Medical School, Okayama University

• 大和 正利

  Faculty Of Pharmaceutical Sciences Okayama University

• 吉川 伸

  Daiichi College Of Pharmaceutical Sciences

• 石川 忠興

  Faculty of Pharmaceutical Sciences, Okayama University

• 永松 朝文

  Faculty Of Pharmaceutical Sciences Okayama University

• 小山 鷹二

  Faculty Of Pharmaceutical Sciences Okayama University

• 石川 忠興

  Faculty Of Pharmaceutical Sciences Okayama University

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