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A novel and practical synthetic route for the total synthesis of lycopene
Authors:Runpu ShenXiaoyue Jiang  Weidong YeXiaohua Song  Luo LiuXuejun Lao  Chunlei Wu
Affiliation:a Department of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, Zhejiang 312000, PR China
b Zhejiang Medicine Co. Ltd., Xinchang Pharmaceutical Factory, Xinchang, Zhejiang 312500, PR China
Abstract:A novel route for the total synthesis of lycopene 1 is described. The synthesis is based on: (i) a condensation between 4,4-dimethoxy-3-methylbutanal 4 and methylenebisphosphonic acid tetraethyl ester 5, leading to the C6-phosphonate 6, followed by (ii) a modified Wittig-Horner reaction between 6 and 6-methyl-5-hepten-2-one 7 producing dimethoxy-3,5,9-triene 8, and (iii) another modified Wittig-Horner reaction between C15-phosphonate 2 and C10-triene dialdehyde 3 producing all-E-lycopene. The synthetic steps are easily operated and practical for the large-scale production.
Keywords:Lycopene   Total synthesis   Wittig-Horner reaction
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