Synthetic Studies on Hennoxazole A with Antivirus Activity

具有抗病毒活性的亨诺恶唑A的合成研究

• 批准号: 06672106
• 负责人: HAMADA Yasumasa
• 金额: $ 1.41万
• 依托单位: Chiba university (1995)Nagoya City University (1994)
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1994
• 资助国家: 日本
• 起止时间: 1994 至 1995
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-06672106/
• 关键词: Hennoxazole; antivivus activity; sgnthetic study; ヘンオキキサゾールA; (S)-1,2,4-ブタントリオール; Wacker酸化

Hennoxazoles (A-D) were isolated by Higa and coworkers from the okinawan sponge, Polyfibrospongia sp. Hennoxazole A has been shown to have interesting antivirus and antiinflammatory activities. The compound possesses a stucturally unique bisoxazole adjacent to a tetrahydropyran/hemiketal and a triene. We hoped to synthesis Hennexazole A via three key intermediates, tetrohydropyran, bisoxazole, and triene moieties. Our work concerned with the attempted synthesis of suitably protected forms of tetrohydropyran and triene moieties.The synthesis of the triene starting from methyl (R)-3-hydroxy-2-methylpropionate was accomplished by cross-coupling of the allyl bromide and the vinyltin using palladium.The methyl ketone, the ring opened form of the tetrahydropyran/hemiketal moiety was synthesized from (S)-1,2,4-butanetriol in several steps.Conversion of the above methyl ketone to the tetrahydropyran/hemiketal is actively underway.

Higa 及其同事从冲绳海绵（多纤维海绵属 sp.） 中分离出亨诺恶唑 (A-D)。亨诺恶唑 A 已被证明具有有趣的抗病毒和抗炎活性。该化合物具有结构独特的双恶唑，与四氢吡喃/半缩酮和三烯相邻。我们希望通过三个关键中间体：四氢吡喃、双恶唑和三烯部分来合成亨内唑 A。我们的工作涉及尝试合成适当保护形式的四氢吡喃和三烯部分。从(R)-3-羟基-2-甲基丙酸甲酯开始合成三烯是通过使用钯将烯丙基溴和乙烯基锡交叉偶联来完成的。甲基酮是甲基酮的开环形式。 四氢吡喃/半缩酮部分由(S)-1,2,4-丁三醇通过几个步骤合成。上述甲基酮向四氢吡喃/半缩酮的转化正在进行中。