Cyanophthalide Annulation with 4-(5-Alkoxy-2-furyl)-3-buten-2-one. Application to the Synthesis of a (Naphtho)pyrano-γ-lactone

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概要

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• Reaction of lithiated 3-cyano-1(3H)-isobenzofuranone (7) with 5-substituted 2-furfuralacetones 6a-c and subsequent O-methylation of the resulting naphthohydroquinones afforded 2-acetyl-3-furylnaphthalenes 8a-c in good yields. Annulation of the dialkoxyphthalides 12a, b with 6a could also be carried out to give 13a, b. The 5-tert-butoxy-2-furyl compounds were stereoselectively transformed into (1R^*, 3R^*, 4R^*)-pyrano-γ-lactones 16a, 18a, b in high yields by a modification of the Kraus method (LiAlH_4 reduction followed by treatment of the product carbinol with p-toluenesulfonic acid (TsOH) in acetonitrile and then with 1,8-diazabicyclo[5.4.0]undec-7-ene in toluene at low temperatures). The 5-methoxy-2-furyl compound 9b also afforded 16a stereoselectively in one step (treatment with TsOH), but this compound was less effective as a substrate of the pyrano-γ-lactone annulation since a side reaction leading to the spiro-γ-lactone 17 became significant. The 5-phenylthio compound 9c failed to give 16a under a variety of conditions.

• 公益社団法人日本薬学会の論文
• 1986-08-25

著者

• 野村 敬一

  Faculty of Pharmaceutical Sciences, Toyama Medical Pharmaceutical University

• 野村 敬一

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 吉井 英一

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 吉井 英一

  富山医科薬科大学薬学部

• 堀 耕造

  Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University

• 岡崎 浩輔

  Facutly of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University

• 岡崎 浩輔

  富山医薬大・薬

• 堀 耕造

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

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