Tetrahedron

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 …

M Alami, S Gueugnot, E Domingues, G Linstrumelle

Index: Alami, Mouad; Gueugnot, Sylvie; Domingues, Elisa; Linstrumelle, Gerard Tetrahedron, 1995 , vol. 51, # 4 p. 1209 - 1220

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Citation Number: 65

Abstract

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.

~65%

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