基于α-叔碳-β,γ-不饱和醛的制备全合成番茄红素  

Total synthesis of lycopene based on preparation method ofβ,γ-unsaturated aldehyde withα-tertiary center

作　　者：谭奇坤 陈果[1] 彭青霞 张伟坚 晏日安[1] TAN Qikun;CHEN Guo;PENG Qingxia;ZHANG Weijian;YAN Rian(Department of Food Science and Engineering,Jinan University,Guangzhou 510000,Guangdong,China;Center for Disease Control and Prevention of Zengcheng District in Guangzhou,Guangzhou 510000,Guangdong,China)

机构地区：[1]暨南大学食品科学与工程系,广东广州510000 [2]广州市增城区疾病预防控制中心,广东广州510000

出　　处：《精细化工》2020年第3期561-566,共6页Fine Chemicals

基　　金：广州市科技计划项目(201903010070)。

摘　　要：将一种α-取代-α,β-不饱和醛的制备方法应用于番茄红素(Ⅵ)的全合成中,通过该法以廉价的原料假性紫罗兰酮(Ⅰ)制备了2,6,10-三甲基-3,5,9-十一烷三烯-1-醛(Ⅱ),然后与四乙基亚甲基二磷酸酯(Ⅲ)经过Wittig-Horner反应得到关键中间体3,7,11-三甲基-1,4,6,10-四烯十二烷基膦酸二乙酯(Ⅳ),最终和2,7-二甲基-2,4,6-辛三烯-1,8-二醛(Ⅴ)进行Wittig-Horner反应、转位异构合成全反式番茄红素。反应共经历3步线性反应,总产率为37.0%。最终产物的结构采用IR、HRMS和NMR进行确证。A method to prepareα,β-unsaturated aldehyde withα-tertiary center was used to synthesize lycopene(Ⅵ).Firstly,pseudoionone(Ⅰ),a low cost raw material,was adopted to synthesize 2,6,10-trimethyl-3,5,9-undectrienyl-1-aldehyde(Ⅱ).Then,key intermediate,diethyl(3,7,11-trimethyldodeca-1,4,6,10-tetraenyl)phosphonate(Ⅳ)was obtained by a Wittig-Horne reaction between aldehydeⅡand tetraethyl methylenediphosphonate(Ⅲ).Finally,a Wittig-Horner reaction between compoundⅣand 2,7-dimethylocta-2,4,6-triene-1,8-dialdehyde(Ⅴ),subsequent rearrangement of isomers led to all-E lycopene.The synthesis of lycopene was only 3 steps with a total yield of 37.0%.The targeted product was characterized by IR,HRMS and NMR techniques.

关 键 词：番茄红素 α-叔碳-β γ-不饱和醛 WITTIG-HORNER反应 食品化学品 

分 类 号：TS202.3[轻工技术与工程—食品科学] TS264.4[轻工技术与工程—食品科学与工程]