2,6-cyclolycopene-1,5-diol: Total synthesis of a naturally occurring oxidation product of lycopene

Article abstract of DOI:10.1016/S0040-4020(98)00564-X

2,6-Cyclolycopene-1,5-diol (3) was synthesized in 9 steps starting from α-terpinyl acetate (11). This represents the first total synthesis of an oxidative metabolite of lycopene (2). The synthesis was performed according to a C₁₅ + C₁₀ + C₁₅ = C₄₀ strategy using the Wittig olefination to couple the end groups to the central building block. An intramolecular aldol addition was used to introduce two new stereocenters with a defined relative stereochemistry.