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

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.