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Synlett 1997; 1997(7): 771-772
DOI: 10.1055/s-1997-5746
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An Efficient Synthesis of Conjugated Trienoic Acids via Stille Cross Coupling Reaction of (E)-1,2-Bis(tributylstannyl)ethylene

Jérôme Thibonnet1 , Mohamed Abarbri1 , Jean-Luc Parrain2 , Alain Duchêne1
  • 1Laboratoire de Physicochimie des Interfaces et des Milieux Réactionnels, Faculté des Sciences de Tours, Parc de Grandmont, 37200 Tours (France)
  • 2Laboratoire de Synthèse Organique associé au CNRS (ESA 6009), Faculté des Sciences de Saint Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20 (France), e-mail: jl.parrain@lso.u-3mrs.fr
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Publication History

Publication Date:
31 December 2000 (online)

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Stereoselective construction of conjugated trienoic acids was achieved through two successive Stille reactions, coupling as the first step (E)-1,2-bis(tributylstannyl)ethylene and tributylstannyl-3-iodoalk-2-enoates. The second step can be conducted by two different routes: 1) cross-coupling of vinyltin reagents and tributylstannyl 5-iodopenta-2,4-dienoates generated by iododestannylation of stannyldienes 2.

conjugated trienoic acids - Stille cross-coupling reaction - vinyltin reagents - (E)-1,2-bis(tributylstannyl)ethene - iodo vinylic substitution