A New Methodology to Key Intermediates for Synthesizing Polyene Compounds

Article abstract of DOI:10.1016/S0040-4020(01)96004-1

ω-Alkoxy-(2E,4E)-dienoates, ω-oxo-(2E,4E)-dienoates and δ-oxo-α,β:γ,δ-dienones were prepared according to a new methodology shown in scheme I.High yield and high stereoselectivity were achieved by using transition metal catalyzed isomerization of ynoates or ynones instead of using Wittig-Horner-wadsworth-Emmons reaction to constitute the diene moiety.The usefulness of this methodology was demonstrated by the preparation of important synthetic precursors to polyene compounds and natural products such as 10-<(tetrahydropyran-2'-yl)oxy>-(2E,4E)-decadienoates, methyl 8-<(tetrahydropyran-2'-yl)oxy>-(2E,4E)-octadienoate, methyl 10-benzyloxy-(2E,4E)-decadienoate, 6-oxo-(2E,4E)-tetradecadienal, methyl 8-oxo-(2E,4E)-octadienoate, and retrofractamide A.