基于CuBr·SMe_2氧化构筑碳碳键为关键反应步骤研究去氧五味子素、TellimagrandinI和土楠酸H的全合成及构效关系
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摘要
碳碳键的偶联一直是合成化学家们关注的热点，目前合成碳碳键的方法主要有Kharasch反应、Negishi反应、Stille反应，Suzuki反应等，这些反应的特点是以稀有金属Pd、Ti等作为催化剂来完成偶联反应。但经过多年对Pd、Ti等金属偶联反应研究，人们逐渐认识到这些金属催化剂的一些缺点，如毒性较大、价格较高以及对不稳定且剧毒的有机磷配体的依赖性等。为了寻找廉价而且低毒的催化剂，在最近20年里，人们将研究的对象转移到廉价易得的Cu催化剂上。近五年，剑桥大学Spring小组利用铜试剂(CuBr·SMe_2)开发了3种构建C-C键的新方法，为了考察该3种新方法在天然产物全合成中的应用，本论文以铜试剂(CuBr·SMe_2)氧化构建碳-碳键为关键反应步骤，对去氧五味子素、Tellimagrandin I和土楠酸H的全合成及构效关系进行了系统研究，主要结果如下：
1．利用铜试剂氧化构建碳碳键的新方法，完成了关键步骤的两次偶联反应，最终合成了去氧五味子素，总产率为14%。该合成方法具有路线较短、原料廉价易得、合成方法简单，所用试剂对环境友好等优点。
采用ArrayScan高内涵筛选分析技术测试了去氧五味子素及其合成中间体2-62～2-65对人骨肉瘤细胞(U2OS)增殖的影响和抗癌活性，结果表明：去氧五味子素和中间体2-63a/2-63b、2-64a、2-65a对细胞增值的抑制效果不明显，但是中间体2-62能够致使细胞明显病变，且对处于正在进行有丝分裂的细胞效果更加明显。因此，化合物2-62可以作为有丝分裂抑制剂，通过抑制细胞分裂减弱人骨肉瘤细胞(U2OS)增殖。采用Sulforhodamine B比色筛选法测试了所有供试化合物对U2OS人骨肉瘤细胞毒性的影响，化合物2-62仍然表现出了良好的活性，其IC_(50)值为43μM；去氧五味子素和化合物2-63表现出较弱的细胞毒性，其IC_(50)值分别为127μM和166μM。
2．通过简短的5步反应，以Rieke Zn﹡和CuBr·SMe_2组成的催化体系催化合成了关键中间体，最终完成了天然产物Tellimagrandin I的全合成，总收率为38%。为了研究Tellimagrandin I的构效关系，还合成了Tellimagrandin I的类似物及含HHDP骨架的中环化合物。
采用ArrayScan高内涵筛选分析技术测试了Tellimagrandin I及其类似物的细胞毒性，抗氧化还原性和蛋白沉淀。具体结果如下：①天然产物Tellimagrandin I的细胞毒性比不含中环HHDP的化合物3-38和3-39强的多，据此推测，中环HHDP骨架对该类化合物的活性起着重要的作用；②中间体3-46表现出比Tellimagrandin I更强的细胞毒性，其结构比Tellimagrandin I简单，合成更为容易；③化合物3-47和3-48在高浓度时表现出较低的细胞毒性，但显示出较强的抗氧化还原能力，有望改造为氧化还原试验的探针。
3．以3-丁炔-1-醇为起始原料，通过5步反应，高效率的合成了中间体4-43，并探索了包括Spring小组发展的新方法、Stille偶联反应和Stille-Kellyn等偶联反应构筑关键中间体4-45，为最终实现土楠酸H的全合成奠定了坚实的基础。
采用剑桥大学Spring小组发展的构筑碳碳键的3种新方法为关键反应步骤，顺利实现了去氧五味子素和Tellimagrandin I全合成，这不仅扩展了上述新方法的应用范围，而且为合成这两类天然产物提供了高效简洁的合成途径。此外，这3种方法具有原料廉价易得，对环境友好等优点。
对去氧五味子素、Tellimagrandin I和土楠酸H的全合成及其构效关系研究结果不但为医药上合成这些具有生物活性的天然产物提供了简洁经济的方法和全新的思路，而且为人们研究这3类化合物的构效关系提供了理论依据和技术指导，具有十分重要的理论和应用价值。
The formation of C-C bond is one of the most important processes in organicchemistry.The major methods for the C-C coupling include Kharasch reaction、Negishireaction、Stille reaction、Suzuki reaction and so on. But their applications are restricted due todrawbacks such as poor yields、poor selectivity and impracticality on large scale.Further more,expensive and highly toxic heavy metal is required. However, there is an increasing of theapplication of the copper-agents oxidation in C-C bond formation due to it is goodselectivity、inexpensive and good to our environment.The Spring goup has developed threemethods for the formation of C-C bond based on copper reagents recently.So,this dissertationaims at the total syntheis and biological profiling of Deoxyschizandrin、Tellimagrandin I andEndiandric acid H based on this three new methods.The primary results are as follows:
1. we have described a concise total synthesis of Deoxyschizandrin based around twokey steps which both utilised organocuprate oxidation methods developed within ourgroup.The first was the assembly a sterically congested aryl-substituted1,3diene with a highlevel of geometric purity (which was subsequently progressed to the methyl-substitutedbutane motif present in the final product) by the stereoselective homocoupling of analkenyl-organocuprate. The second key step was biaryl bond formation with concomitantmedium ring construction by the oxidation of an intramolecular aryl-organocuprate. Theseresults provide a clear illustration of the usefulness of these copper-mediated couplingmethodologies in complex molecule synthesis.
In addition, we present the results of biological studies exploring the ability ofDeoxyschizandrin and synthetic precursors lacking the medium ring biaryl unit to inhibit theproliferation of a human cancer cell line.This led to the discovery of2-62, a novel,non-natural derivative which inhibited the proliferation of human osteosarcoma cells.
2. We have shown that Tellimagrandin I can be synthesized in five linear steps with anoverall yield of38%using an atropdiastereoselective oxidative biaryl coupling as the key step.Tellimagrandin I and analogues were used to explore the SAR of Ellagitannin components.
We have adapted several rapid assays for benchmarking Ellagitannin activity in two of its most commonly associated biological properties and shown how this translates into acellular setting.Cytotoxicity increased with ring size and was lost with the removal of themedium ring.This data correlated with the redox activity but not with the ability to precipitateprotein, suggesting the importance of the former in Ellagitannin bioactivity.Additionally,anew analogue (3-46) was identified which was significantly more potent than TellimagrandinI but structurally and synthetically simpler. Our data suggests that the biological activity ofEllagitannins can be optimised for the required properties and that complex scaffolds may notbe required to exert this activity. We have uncovered a novel class of redox modulating agents(3-47&3-48) which are only weakly cytotoxic at high concentrations and which may findapplications as redox probes.
3. The critical precursor4-43towards the total synthesis of Endiandric acid H has beenaccomplished from3-butyn-1-ol in five linear steps with an overall yield of37%. Meanwhile,Many methods have been tested for the synthesis of4-45which gave foundation for the totalsynthesis of Endiandric acid H.
The synthesis and biological profiling of Deoxyschizandrin,Tellimagrandin I andEndiandric acid H will contribute significantly to the industrial application.
1．利用铜试剂氧化构建碳碳键的新方法，完成了关键步骤的两次偶联反应，最终合成了去氧五味子素，总产率为14%。该合成方法具有路线较短、原料廉价易得、合成方法简单，所用试剂对环境友好等优点。
采用ArrayScan高内涵筛选分析技术测试了去氧五味子素及其合成中间体2-62～2-65对人骨肉瘤细胞(U2OS)增殖的影响和抗癌活性，结果表明：去氧五味子素和中间体2-63a/2-63b、2-64a、2-65a对细胞增值的抑制效果不明显，但是中间体2-62能够致使细胞明显病变，且对处于正在进行有丝分裂的细胞效果更加明显。因此，化合物2-62可以作为有丝分裂抑制剂，通过抑制细胞分裂减弱人骨肉瘤细胞(U2OS)增殖。采用Sulforhodamine B比色筛选法测试了所有供试化合物对U2OS人骨肉瘤细胞毒性的影响，化合物2-62仍然表现出了良好的活性，其IC_(50)值为43μM；去氧五味子素和化合物2-63表现出较弱的细胞毒性，其IC_(50)值分别为127μM和166μM。
2．通过简短的5步反应，以Rieke Zn﹡和CuBr·SMe_2组成的催化体系催化合成了关键中间体，最终完成了天然产物Tellimagrandin I的全合成，总收率为38%。为了研究Tellimagrandin I的构效关系，还合成了Tellimagrandin I的类似物及含HHDP骨架的中环化合物。
采用ArrayScan高内涵筛选分析技术测试了Tellimagrandin I及其类似物的细胞毒性，抗氧化还原性和蛋白沉淀。具体结果如下：①天然产物Tellimagrandin I的细胞毒性比不含中环HHDP的化合物3-38和3-39强的多，据此推测，中环HHDP骨架对该类化合物的活性起着重要的作用；②中间体3-46表现出比Tellimagrandin I更强的细胞毒性，其结构比Tellimagrandin I简单，合成更为容易；③化合物3-47和3-48在高浓度时表现出较低的细胞毒性，但显示出较强的抗氧化还原能力，有望改造为氧化还原试验的探针。
3．以3-丁炔-1-醇为起始原料，通过5步反应，高效率的合成了中间体4-43，并探索了包括Spring小组发展的新方法、Stille偶联反应和Stille-Kellyn等偶联反应构筑关键中间体4-45，为最终实现土楠酸H的全合成奠定了坚实的基础。
采用剑桥大学Spring小组发展的构筑碳碳键的3种新方法为关键反应步骤，顺利实现了去氧五味子素和Tellimagrandin I全合成，这不仅扩展了上述新方法的应用范围，而且为合成这两类天然产物提供了高效简洁的合成途径。此外，这3种方法具有原料廉价易得，对环境友好等优点。
对去氧五味子素、Tellimagrandin I和土楠酸H的全合成及其构效关系研究结果不但为医药上合成这些具有生物活性的天然产物提供了简洁经济的方法和全新的思路，而且为人们研究这3类化合物的构效关系提供了理论依据和技术指导，具有十分重要的理论和应用价值。
The formation of C-C bond is one of the most important processes in organicchemistry.The major methods for the C-C coupling include Kharasch reaction、Negishireaction、Stille reaction、Suzuki reaction and so on. But their applications are restricted due todrawbacks such as poor yields、poor selectivity and impracticality on large scale.Further more,expensive and highly toxic heavy metal is required. However, there is an increasing of theapplication of the copper-agents oxidation in C-C bond formation due to it is goodselectivity、inexpensive and good to our environment.The Spring goup has developed threemethods for the formation of C-C bond based on copper reagents recently.So,this dissertationaims at the total syntheis and biological profiling of Deoxyschizandrin、Tellimagrandin I andEndiandric acid H based on this three new methods.The primary results are as follows:
1. we have described a concise total synthesis of Deoxyschizandrin based around twokey steps which both utilised organocuprate oxidation methods developed within ourgroup.The first was the assembly a sterically congested aryl-substituted1,3diene with a highlevel of geometric purity (which was subsequently progressed to the methyl-substitutedbutane motif present in the final product) by the stereoselective homocoupling of analkenyl-organocuprate. The second key step was biaryl bond formation with concomitantmedium ring construction by the oxidation of an intramolecular aryl-organocuprate. Theseresults provide a clear illustration of the usefulness of these copper-mediated couplingmethodologies in complex molecule synthesis.
In addition, we present the results of biological studies exploring the ability ofDeoxyschizandrin and synthetic precursors lacking the medium ring biaryl unit to inhibit theproliferation of a human cancer cell line.This led to the discovery of2-62, a novel,non-natural derivative which inhibited the proliferation of human osteosarcoma cells.
2. We have shown that Tellimagrandin I can be synthesized in five linear steps with anoverall yield of38%using an atropdiastereoselective oxidative biaryl coupling as the key step.Tellimagrandin I and analogues were used to explore the SAR of Ellagitannin components.
We have adapted several rapid assays for benchmarking Ellagitannin activity in two of its most commonly associated biological properties and shown how this translates into acellular setting.Cytotoxicity increased with ring size and was lost with the removal of themedium ring.This data correlated with the redox activity but not with the ability to precipitateprotein, suggesting the importance of the former in Ellagitannin bioactivity.Additionally,anew analogue (3-46) was identified which was significantly more potent than TellimagrandinI but structurally and synthetically simpler. Our data suggests that the biological activity ofEllagitannins can be optimised for the required properties and that complex scaffolds may notbe required to exert this activity. We have uncovered a novel class of redox modulating agents(3-47&3-48) which are only weakly cytotoxic at high concentrations and which may findapplications as redox probes.
3. The critical precursor4-43towards the total synthesis of Endiandric acid H has beenaccomplished from3-butyn-1-ol in five linear steps with an overall yield of37%. Meanwhile,Many methods have been tested for the synthesis of4-45which gave foundation for the totalsynthesis of Endiandric acid H.
The synthesis and biological profiling of Deoxyschizandrin,Tellimagrandin I andEndiandric acid H will contribute significantly to the industrial application.
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