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番茄红素的全合成

马文鑫, 梁智平, 王渭军, 胡四平, 沈润溥, 吴春雷

马文鑫, 梁智平, 王渭军, 胡四平, 沈润溥, 吴春雷. 番茄红素的全合成[J]. 中国药科大学学报, 2013, 44(5): 390-393. DOI: 10.11665/j.issn.1000-5048.20130502
引用本文: 马文鑫, 梁智平, 王渭军, 胡四平, 沈润溥, 吴春雷. 番茄红素的全合成[J]. 中国药科大学学报, 2013, 44(5): 390-393. DOI: 10.11665/j.issn.1000-5048.20130502
MA Wenxin, LIANG Zhiping, WANG Weijun, HU Siping, SHEN Runpu, WU Chunlei. Total synthesis of lycopene[J]. Journal of China Pharmaceutical University, 2013, 44(5): 390-393. DOI: 10.11665/j.issn.1000-5048.20130502
Citation: MA Wenxin, LIANG Zhiping, WANG Weijun, HU Siping, SHEN Runpu, WU Chunlei. Total synthesis of lycopene[J]. Journal of China Pharmaceutical University, 2013, 44(5): 390-393. DOI: 10.11665/j.issn.1000-5048.20130502

番茄红素的全合成

基金项目: 国家自然科学基金资助项目(No.21176156)

Total synthesis of lycopene

  • 摘要: 设计完成了一条新的全反式番茄红素全合成路线:由4,8-二甲基-3,7-壬二烯-1-醛( 2 )与丙醛( 3 )经Aldol缩合反应制备关键中间体2,6,10-三甲基-2,5,9-十一烷三烯-1-醛( 4 ),再与偕二膦酸酯( 5 )经Wittig-Horner反应得到3,7,11-三甲基-1,3,6,10-四烯十二烷基膦酸二乙酯( 6 ),最后与十碳双醛( 7 )反应得到全反式番茄红素( 1 ),总收率为58.7%。与以往的全合成路线相比,具有步骤少、工艺简单、反应收率高等特点,具有较大的工业化生产潜力。
    Abstract: A novel route to the total synthesis of lycopene was described. The synthesis was based on the following three steps: (i)the aldol condensation between 4, 8-dimethylnona-3, 7-dienal( 2 )and propionaldehyde( 3 )led to the key intermediate, 2, 6, 10-trimethylundeca-2, 5, 9-trienal( 4 ); (ii)3, 7, 11-trimethyldodeca-1, 3, 6, 10-tetraenylphosphonate( 6 )could be prepared via the modified Wittig-Horner reaction between (4) and methylenebisphosphonic acid tetraethyl ester( 5 ); (iii)another modified Wittig-Horner reaction between( 6 )and C10-triene dialdehyde( 7 )could produce all-E-lycopene( 1 ). The overall yield was 58. 7%. This approach offers many advantages including less steps, simple operations, high-yielding compared with the conventional synthetic routes, and exhibits a potential for large-scale production.
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出版历程
  • 刊出日期:  2013-10-24

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