An efficient synthesis of 1,3(E),5(Z), 1,3(E),5(E)and 1,3(Z),5(Z)-trienes: Application to the synthesis of galbanolenes and (9Z,11E)-9,11,13-tetradecatrien-1-yl acetate

Article abstract of DOI:10.1016/0040-4020(94)00991-3

The (Pd-Cu)-catalyzed reactions of trimethylsilyl acetylene with (E) or (Z)-chloroenynes, or 1-chloro-(1E,3E)-dienes, followed by desilylation and zinc-reduction of the triple bonds led respectively to (3E,5Z), (3Z,5Z) and (3E,5E)-trienes. Application to the syntheses of galbanolenes and (9Z,11E)-9,11,13-tetradecatrien-1-yl acetate has been realized.