Syntheses of Hydroxymethyl-carotenoids Using Vinyl-Anions Generated by the Shapiro-Reaction

Article abstract of DOI:10.1002/hlca.19830660418

A versatile synthesis of hydroxymethyl-carotenoids with β- or ε-end groups is presented.It makes use of the reactive vinyl anions prepared by the Shapiro-reaction from (phenylsulfonyl)hydrazones of polyenones and their smooth 1,2-addition to polyenals.Thus, e.g. (3R,6'R)-β,ε-carotene-3,19-diol (72), an optically active model compound structurally very close to loroxanthin (1), has been sinthesized.