1.2.4- Trienes synthesis

F. G. Prendergast, R. P. Haugland, and P. J. Callahan, l-[4-(Trimethylamino)phenyl]-6-phenylhexa-l,3,5-triene synthesis, fluorescence properties, and use as a fluorescence probe of lipid bilayers, Biochemistry 20, 7333-7338 (1983). 

Equally interesting is the triene synthesis from propargylic bromides, bis(iodozincio)methane, and allyl halides. 

The presence of a hetcroatom in the tether linking the diene and dienophile units often simplifies triene synthesis, since it provides a point at which the triene may be disconnected into simpler fragments. The diene- and dienophile-containing subunits may be joined using routine synthetic transformations such as esterification, etherification and amide formation. 

Triene Synthesis. Like other vinylsilanes, 1-trimethylsilyl-1,3-hutadiene can be used in a Hiyama coupling reaction with vinyl iodides (eq 8)7... 

Jourdain, P., Philipart, F., Dumeunier, R., and Marko, I.E. (2009) Pentadienyl sulfoxide in triene synthesis. Efficient assembly of the Northern fragment of polycavemoside A. Tetrahedron Lett., 50, 3366-3370. 

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