A novel and practical synthetic route for the total synthesis of lycopene

作者:Shen Runpu; Jiang Xiaoyue; Ye Weidong; Song Xiaohua; Liu Luo; Lao Xuejun; Wu Chunlei*
来源:Tetrahedron, 2011, 67(31): 5610-5614.
DOI:10.1016/j.tet.2011.05.104

摘要

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.

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