Total synthesis of lycopene based on dodecatrienal
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(Department of Food Science and Engineering, Jinan University, Guangzhou, Guangdong 510632, China)

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    Abstract:

    Diethyl \[(1E,3E,5E)-2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl\]phosphonate (9) was synthesized via a condensation between tetraethyl methylenebis(phosphonate) (7) and 6,10-dimethyl-3,5,9-undecatrien-2-one(8) by Wittig-Horner reaction, (3E,5E,7E)-3,8-dimethyldeca-3,5,7-trienedial (5) was prepared from (E)-tetraethyl but-2-ene-1,4-diylbis-(phosphonate)(2) and 4,4-dimethoxy-2-butanone (3) by Wittig-Horner reaction followed by hydrogenation. Lycopene was synthesized from diethyl \[(1E,3E,5E)-2,6,10-trimethylundeca-1,3,5,9-tetraen-1-yl\]phosphonate(9)and(3E,5E,7E)-3,8-dimethyldeca-3,5,7-trienedial(5) by Wittig-Horner reaction,the structure of products was confirmed by NMR, HRMS/GC-MS and IR techniques. The total yield was 16.7%.

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陈果,晏日安,黎海梅,等.基于十二碳烯醛的番茄红素全合成[J].食品与机械英文版,2021,37(3):162-167.

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  • Received:November 29,2020
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  • Online: February 15,2023
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