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布格呋喃体内代谢产物的合成

Synthesis of a new metabolite of buagarofuran(AF-5)

  • 摘要: 布格呋喃(AF-5)是已报道的一类具有抗焦虑活性的精神治疗药物之一,其结构由一个沉香呋喃环骨架和一个正丁基侧链组成。临床药代研究发现其新的代谢产物,推测其结构可能为烷烃链端基的羰酸化产物。为了确证其结构,以中间体(4aR,7R,8aR)-8a-羟基-7-(2-羟丙基-2-基)-4a-甲基八氢萘-2(1氢)-酮为原料,经6步反应,成功合成了目标化合物,总收率16.7%。化合物的结构均经NMR和MS确证。

     

    Abstract: It has been reported that buagarofuran(AF-5)as an anxiolytic drug. It possesses a structural feature including α-agarofuran and the n-butyl side chain. Recently, there is a new metabolite found in clinical study, which is hypothesized that the n-butyl side chain has been oxidized to carboxylic acid. In order to confirm its structure, the target compound was prepared from(4aR, 7R, 8aR)-8a-hydroxy-7-(2-hydroxypropan-2-yl)-4a-methyloctahydronaphthalen-2(1H)-one in a six-step reaction with an overall yield of 16. 7%. The structure is confirmed by NMR and MS.

     

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