Lespedezavirgatol及其衍生物的合成
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摘要
从植物中分离出来的许多2-苯基苯并呋喃类化合物是选择性腺苷A1受体拮抗剂、抗自由基、抗氧化、免疫抑制剂等生理活性物质,具有良好的抗病毒、抗肿瘤或抗菌作用,引起了人们较大的研究兴趣。
天然产物Lespedezavirgatol是从细梗胡枝子分离出来的结构新颖的2-(2,6-二取代苯基)-苯并呋喃化合物,具有氧自由基清除活性。由于它的提取非常困难,产率极低,因此其人工合成就显得非常重要。本文首先对Lespedezavirgatol进行了反合成分析;然后根据所设计的合成路线,完成了其全合成。在此基础上,设计并合成了5个新型2-(2,6-二取代苯基)-苯并呋喃化合物,并考察了两种不同的催化体系Pd(PPh3)Cl2-CuI和[Cu(phen)(PPh3)2]NO3-Cs2CO3对形成苯并呋喃骨架的影响。
1. Lespedezavirgatol的全合成:
从焦性没食子酸和3,4-二甲氧基苯酚出发,分别合成了4-碘代-2-甲氧基苯二酚和2-乙炔基-3,4-二甲氧基-1-(甲氧基甲氧基)苯;这两个中间产物在催化剂的作用下发生Sonogashira偶联,生成苯并呋喃环。连苯三酚的甲基化反应和3,4-二甲氧基苯酚在2-位上的碘代反应是全合成过程中的两个关键反应。
2. 2-(2,6-二取代苯基)-苯并呋喃衍生物的合成
设计合成了一系列的2-(2,6-二取代苯基)-苯并呋喃衍生物化合物。制备了催化剂[Cu(phen)(PPh3)2]NO3;研究了自制催化剂和Pd(PPh3)Cl2对含有供电子基团与吸电子基团的邻碘代苯酚与苯乙炔生成苯并呋喃环的影响;所合成的四个新型苯并呋喃化合物经1HNMR、13CNMR、MS和元素分析所证实。
Many 2-phenylbenzofuran derivatives isolated from plants or Chinese herbal medicines are biologically active components which are used for antagonist of selective adenosine A1 receptor, anti-radicals, anti-radicals and immunosuppressive agents with good physiological activities, these compounds also performed well in anti-virus, anti-tumor, and antifungal aspects [1-6] which attracted people’s attention for a long time.
Natural product Lespedezavirgatol is a new benzo[b]furan derivatives isolated from lespedeza virgata (Thunb.) with strong oxygen radical absorbance capacity. Because the extraction procedure is very difficult and usually has a low yield, so chemical synthesis becomes of great importance. In this paper, we first carried out retrosynthetic analysis for the synthesis of lespedezavirgatol; then by the synthetic route, we completed total synthesis of lespedezavirgatol. Based on the above work, we designed and synthesized five 2-(2’, 6’-disubstituted phenyl)-benzo[b]furan derivatives with novel structure, and explored the effect of two kinds of catalyst Pd(PPh3)Cl2-CuI and [Cu(phen)(PPh3)2]NO3-Cs2CO3 on the formation of benzo[b]furan skeleton.
1. The total synthesis of Lespedezavirgatol
Starting from pyrogallic acid and 3,4-dimethoxyphenol, we get 4-iodo-2- methoxybenzene-1,3-diol and 2-ethynyl-3,4-dimethoxy-1-(methoxymethoxy)benzene. Then via sonogashira cross-coupling cyclization reaction the two intermediate products developed to be benzo[b]furan skeleton in the presence of catalyst. The methylation reaction of pyrogallic acid and iodination of 3,4-dimethoxyphenol on the 2-position are the key steps in the process of total synthesis.
2. The synthesis of 2-(2, 6-disubstituted phenyl) benzo[b]furan compounds
We designed and synthesized a series of 2-(2, 6-disubstituted phenyl) benzo[b]furan. Prepared catalyst [Cu(phen)(PPh3)2]NO3; studied the effect of different catalyst system on the formation of benzo[b]furan skeleton by preparing [Cu(phen)(PPh3)2]NO3 and Pd(PPh3)Cl2 commercially available. All the five compounds’structure have been defined by 1HNMR、13CNMR、MS and elementary analysis.
天然产物Lespedezavirgatol是从细梗胡枝子分离出来的结构新颖的2-(2,6-二取代苯基)-苯并呋喃化合物,具有氧自由基清除活性。由于它的提取非常困难,产率极低,因此其人工合成就显得非常重要。本文首先对Lespedezavirgatol进行了反合成分析;然后根据所设计的合成路线,完成了其全合成。在此基础上,设计并合成了5个新型2-(2,6-二取代苯基)-苯并呋喃化合物,并考察了两种不同的催化体系Pd(PPh3)Cl2-CuI和[Cu(phen)(PPh3)2]NO3-Cs2CO3对形成苯并呋喃骨架的影响。
1. Lespedezavirgatol的全合成:
从焦性没食子酸和3,4-二甲氧基苯酚出发,分别合成了4-碘代-2-甲氧基苯二酚和2-乙炔基-3,4-二甲氧基-1-(甲氧基甲氧基)苯;这两个中间产物在催化剂的作用下发生Sonogashira偶联,生成苯并呋喃环。连苯三酚的甲基化反应和3,4-二甲氧基苯酚在2-位上的碘代反应是全合成过程中的两个关键反应。
2. 2-(2,6-二取代苯基)-苯并呋喃衍生物的合成
设计合成了一系列的2-(2,6-二取代苯基)-苯并呋喃衍生物化合物。制备了催化剂[Cu(phen)(PPh3)2]NO3;研究了自制催化剂和Pd(PPh3)Cl2对含有供电子基团与吸电子基团的邻碘代苯酚与苯乙炔生成苯并呋喃环的影响;所合成的四个新型苯并呋喃化合物经1HNMR、13CNMR、MS和元素分析所证实。
Many 2-phenylbenzofuran derivatives isolated from plants or Chinese herbal medicines are biologically active components which are used for antagonist of selective adenosine A1 receptor, anti-radicals, anti-radicals and immunosuppressive agents with good physiological activities, these compounds also performed well in anti-virus, anti-tumor, and antifungal aspects [1-6] which attracted people’s attention for a long time.
Natural product Lespedezavirgatol is a new benzo[b]furan derivatives isolated from lespedeza virgata (Thunb.) with strong oxygen radical absorbance capacity. Because the extraction procedure is very difficult and usually has a low yield, so chemical synthesis becomes of great importance. In this paper, we first carried out retrosynthetic analysis for the synthesis of lespedezavirgatol; then by the synthetic route, we completed total synthesis of lespedezavirgatol. Based on the above work, we designed and synthesized five 2-(2’, 6’-disubstituted phenyl)-benzo[b]furan derivatives with novel structure, and explored the effect of two kinds of catalyst Pd(PPh3)Cl2-CuI and [Cu(phen)(PPh3)2]NO3-Cs2CO3 on the formation of benzo[b]furan skeleton.
1. The total synthesis of Lespedezavirgatol
Starting from pyrogallic acid and 3,4-dimethoxyphenol, we get 4-iodo-2- methoxybenzene-1,3-diol and 2-ethynyl-3,4-dimethoxy-1-(methoxymethoxy)benzene. Then via sonogashira cross-coupling cyclization reaction the two intermediate products developed to be benzo[b]furan skeleton in the presence of catalyst. The methylation reaction of pyrogallic acid and iodination of 3,4-dimethoxyphenol on the 2-position are the key steps in the process of total synthesis.
2. The synthesis of 2-(2, 6-disubstituted phenyl) benzo[b]furan compounds
We designed and synthesized a series of 2-(2, 6-disubstituted phenyl) benzo[b]furan. Prepared catalyst [Cu(phen)(PPh3)2]NO3; studied the effect of different catalyst system on the formation of benzo[b]furan skeleton by preparing [Cu(phen)(PPh3)2]NO3 and Pd(PPh3)Cl2 commercially available. All the five compounds’structure have been defined by 1HNMR、13CNMR、MS and elementary analysis.
引文
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