Abstract
1,2,5,6-Tetrahydro-2,6-cyclo-γ-carotene-1,5-diol, an oxidation product of the pro-vitamin A food carotenoid γ-carotene, was synthesized by a C15 + C10 + C15 double Wittig coupling strategy. The total synthesis involved a key C15-dihydroxyaldehyde synthon derived from (E/Z)-citral, a protected C10-Wittig salt, and (β-ionylideneethyl)triphenylphosphonium chloride (C15-Wittig salt). This synthetic route provides novel access to an oxidation product of γ-carotene that could be potentially formed in humans or biological systems as a consequence of metabolic oxidation.
Key words
hydroxycarotenoids - Wittig reaction - γ-carotene oxidation - carotenoid precursors - epoxide cyclization