吗啡生物碱合成研究
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摘要
吗啡是人类19世纪初叶分离得到的第一个纯单体天然生物碱,具有显著的镇痛功效。时隔百余年,在英国化学家Robinson最终确立了该分子的正确化学结构之后,吗啡生物碱的高效合成以及母体结构的多样性修饰与改造成为了合成化学家、药物化学家的重要研究内容之一,其中具有里程碑意义的吗啡生物碱人工化学合成首次完成于上个世纪50年代。尽管吗啡类生物碱的化学合成已经取得了一系列进展,但是新合成路线与策略的发展一直都是吗啡类生物碱合成研究中的重要内容。本论文主要围绕吗啡生物碱的合成研究,通过若干合成策略的设计,对一些新颖的合成方法进行了目标导向的合成应用探讨,为此类生物碱的形式合成研究提供了不同的途径。该论文主要分为以下两个部分讨论：
第一部分：基于对前人吗啡合成工作的回溯,我们以若干关键策略的运用为分类依据,从“仿生合成、菲环导向的合成、分子内环化导向的合成、环己二烯酮中间体导向的合成、Diels-Alder环加成导向的合成”等方面,重点介绍了吗啡生物碱全合成、形式合成研究中的一些重要进展。
第二部分：针对吗啡生物碱新合成策略的发展,围绕其分子骨架中关键的“六元全碳B环”与“五元氧杂E环”的构建,我们主要以“串联醇解/Oxo-Michael加成反应”与“SmI2促进的还原偶联/去硫化反应”为关键步骤,对吗啡的新合成路线进行了较为深入的探讨,并在此基础上最终实现了吗啡生物碱的形式合成研究。此外,鉴于E环的手性构建在吗啡不对称合成中的重要性,我们还基于“对映选择性去对称化策略”,对潜手性环己二烯酮的“不对称串联醇解/Oxo-Michael加成反应”进行了初步探讨,该方法学的研究为吗啡的对映选择性合成提供了新途径。
Morphine as one of medicinally significant molecules having highly potent opiate analgesic effect was originally isolated from the opium poppy(Papaver sonmiferum) in the very beginning of the nineteenth century. After more than one hundred years, the British chemist Robinson eventually established the correct chemical structure of morphine. Since then, the effective synthesis and structurally diverse modification of morphine and related alkaloids become one of the important research contents of synthetic and medicinal chemists. As one milestone during the chemical synthesis of morphine, its first total synthesis was achieved by M. Gates in1952. Despite the substantial progress in the synthetic studies of morphine alkaloids, the development of novel synthetic strategies and routes has always been one important topic in the synthesis of morphine alkaloids. This dissertation mainly aims at the design and development of some strategies in the synthetic studies of morphine. Focusing on this issue, the target-oriented methodology was investigated, providing the alternative way to the formal synthesis of morphine. The following two parts are included in this thesis:
Part I:With the retrospective analysis for the previous literature reports on the synthesis of morphine alkaloids, some representative achievements are summarized on the basis of the application of key strategies, which mainly included the biomimetic synthesis, the phenanthrene core-oriented synthesis, the intramolecular cyclization-mediated synthesis, the cyclohexadienone-derived synthesis, and Diels-Alder cycloaddition-based synthesis.
Part II:Focusing on the construction of the key "all-carbon six-membered ring B" and "five-membered hetero-ring E" in the molecular skeleton of morphine, we developed a novel synthetic strategy featuring "tandem alcoholysis/oxo-Michael reaction" and "SmI2-mediated reductive coupling/desulfurization reaction" successfully leading to a formal synthesis of morphine. Additionally, considering the importance of asymmetric establishment of ring E for the enantioselective synthesis of morphine, a novel "asymmetric tandem alcoholysis/oxo-Michael addition of prochiral cyclohexadienones" was also preliminarily explored on the basis of the enantioselective desymmetrization. Significantly, this stereocontrolled methodology will provide a new route to the enantioselective synthesis of morphine.
第一部分：基于对前人吗啡合成工作的回溯,我们以若干关键策略的运用为分类依据,从“仿生合成、菲环导向的合成、分子内环化导向的合成、环己二烯酮中间体导向的合成、Diels-Alder环加成导向的合成”等方面,重点介绍了吗啡生物碱全合成、形式合成研究中的一些重要进展。
第二部分：针对吗啡生物碱新合成策略的发展,围绕其分子骨架中关键的“六元全碳B环”与“五元氧杂E环”的构建,我们主要以“串联醇解/Oxo-Michael加成反应”与“SmI2促进的还原偶联/去硫化反应”为关键步骤,对吗啡的新合成路线进行了较为深入的探讨,并在此基础上最终实现了吗啡生物碱的形式合成研究。此外,鉴于E环的手性构建在吗啡不对称合成中的重要性,我们还基于“对映选择性去对称化策略”,对潜手性环己二烯酮的“不对称串联醇解/Oxo-Michael加成反应”进行了初步探讨,该方法学的研究为吗啡的对映选择性合成提供了新途径。
Morphine as one of medicinally significant molecules having highly potent opiate analgesic effect was originally isolated from the opium poppy(Papaver sonmiferum) in the very beginning of the nineteenth century. After more than one hundred years, the British chemist Robinson eventually established the correct chemical structure of morphine. Since then, the effective synthesis and structurally diverse modification of morphine and related alkaloids become one of the important research contents of synthetic and medicinal chemists. As one milestone during the chemical synthesis of morphine, its first total synthesis was achieved by M. Gates in1952. Despite the substantial progress in the synthetic studies of morphine alkaloids, the development of novel synthetic strategies and routes has always been one important topic in the synthesis of morphine alkaloids. This dissertation mainly aims at the design and development of some strategies in the synthetic studies of morphine. Focusing on this issue, the target-oriented methodology was investigated, providing the alternative way to the formal synthesis of morphine. The following two parts are included in this thesis:
Part I:With the retrospective analysis for the previous literature reports on the synthesis of morphine alkaloids, some representative achievements are summarized on the basis of the application of key strategies, which mainly included the biomimetic synthesis, the phenanthrene core-oriented synthesis, the intramolecular cyclization-mediated synthesis, the cyclohexadienone-derived synthesis, and Diels-Alder cycloaddition-based synthesis.
Part II:Focusing on the construction of the key "all-carbon six-membered ring B" and "five-membered hetero-ring E" in the molecular skeleton of morphine, we developed a novel synthetic strategy featuring "tandem alcoholysis/oxo-Michael reaction" and "SmI2-mediated reductive coupling/desulfurization reaction" successfully leading to a formal synthesis of morphine. Additionally, considering the importance of asymmetric establishment of ring E for the enantioselective synthesis of morphine, a novel "asymmetric tandem alcoholysis/oxo-Michael addition of prochiral cyclohexadienones" was also preliminarily explored on the basis of the enantioselective desymmetrization. Significantly, this stereocontrolled methodology will provide a new route to the enantioselective synthesis of morphine.
引文
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