Total synthesis of morphine and related alkaloids (original) (raw)
吗啡全合成是指化学中吗啡样生物碱的合成，描述了天然类生物碱的全合成，其包括可待因，吗啡，，和蒂巴因及其密切相关的半合成类似物丁丙诺啡，氢可酮，，，纳洛酮，纳布啡和羟考酮。 吗啡的结构并不是特别复杂，然而，相邻结合原子的静电极化在整个结构中不均匀交替。这种“不一致的连接性”使得键的形成更加困难，并且因此使应用于该分子家族的任何合成策略明显的复杂化。 首次全合成由美國化學家于1952年完成，并被视为这个领域中的经典之作。该合成总共用了31个步骤，并且总产率有0.06％。Kenner C. Rice的氢可酮合成是最有效的，用了14个步骤并且有30％的总产率。 此后，许多化学家提出了新的合成路线，其中值得注意的有以下研究者率领的团队所提出的路线：赖斯、埃文斯、富克斯、帕克、奥尔曼、木泽尔·特劳纳、怀特、泰伯、特罗斯特、福山、吉尤和斯托克。
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| dbo:abstract | Synthesis of morphine-like alkaloids in chemistry describes the total synthesis of the natural morphinan class of alkaloids that includes codeine, morphine, oripavine, and thebaine and the closely related semisynthetic analogs methorphan, buprenorphine, hydromorphone, hydrocodone, isocodeine, naltrexone, nalbuphine, oxymorphone, oxycodone, and naloxone. The structure of morphine is not particularly complex, however the electrostatic polarization of adjacent bonded atoms does not alternate uniformly throughout the structure. This "dissonant connectivity" makes bond formation more difficult and therefore significantly complicates any synthetic strategy that is applied to this family of molecules. The first morphine total synthesis, devised by Marshall D. Gates, Jr. in 1952 remains a widely used example of total synthesis. This synthesis took a total of 31 steps and proceeded in 0.06% overall yield. The hydrocodone synthesis of Kenner C. Rice is one of the most efficient and proceeds in 30% overall yield in 14 steps. At 9 steps, the Barriault route is the shortest to date, but contains a number of low-yielding steps and is racemic. Several other syntheses were reported, notably by the research groups of Evans, Fuchs, Parker, Overman, Mulzer-Trauner, White, Taber, Trost, Fukuyama, Guillou, Stork, Magnus, Smith, and Barriault. (en) 吗啡全合成是指化学中吗啡样生物碱的合成，描述了天然类生物碱的全合成，其包括可待因，吗啡，，和蒂巴因及其密切相关的半合成类似物丁丙诺啡，氢可酮，，，纳洛酮，纳布啡和羟考酮。 吗啡的结构并不是特别复杂，然而，相邻结合原子的静电极化在整个结构中不均匀交替。这种“不一致的连接性”使得键的形成更加困难，并且因此使应用于该分子家族的任何合成策略明显的复杂化。 首次全合成由美國化學家于1952年完成，并被视为这个领域中的经典之作。该合成总共用了31个步骤，并且总产率有0.06％。Kenner C. Rice的氢可酮合成是最有效的，用了14个步骤并且有30％的总产率。 此后，许多化学家提出了新的合成路线，其中值得注意的有以下研究者率领的团队所提出的路线：赖斯、埃文斯、富克斯、帕克、奥尔曼、木泽尔·特劳纳、怀特、泰伯、特罗斯特、福山、吉尤和斯托克。 (zh) |
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| rdfs:comment | 吗啡全合成是指化学中吗啡样生物碱的合成，描述了天然类生物碱的全合成，其包括可待因，吗啡，，和蒂巴因及其密切相关的半合成类似物丁丙诺啡，氢可酮，，，纳洛酮，纳布啡和羟考酮。 吗啡的结构并不是特别复杂，然而，相邻结合原子的静电极化在整个结构中不均匀交替。这种“不一致的连接性”使得键的形成更加困难，并且因此使应用于该分子家族的任何合成策略明显的复杂化。 首次全合成由美國化學家于1952年完成，并被视为这个领域中的经典之作。该合成总共用了31个步骤，并且总产率有0.06％。Kenner C. Rice的氢可酮合成是最有效的，用了14个步骤并且有30％的总产率。 此后，许多化学家提出了新的合成路线，其中值得注意的有以下研究者率领的团队所提出的路线：赖斯、埃文斯、富克斯、帕克、奥尔曼、木泽尔·特劳纳、怀特、泰伯、特罗斯特、福山、吉尤和斯托克。 (zh) Synthesis of morphine-like alkaloids in chemistry describes the total synthesis of the natural morphinan class of alkaloids that includes codeine, morphine, oripavine, and thebaine and the closely related semisynthetic analogs methorphan, buprenorphine, hydromorphone, hydrocodone, isocodeine, naltrexone, nalbuphine, oxymorphone, oxycodone, and naloxone. Several other syntheses were reported, notably by the research groups of Evans, Fuchs, Parker, Overman, Mulzer-Trauner, White, Taber, Trost, Fukuyama, Guillou, Stork, Magnus, Smith, and Barriault. (en) |
| rdfs:label | Total synthesis of morphine and related alkaloids (en) 吗啡全合成 (zh) |
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