Journal of Organic Chemistry p. 5312 - 5323 (1990)
Update date:2022-08-03
Topics: Synthesis Chemical reactions Organic synthesis Functional group Short synthesis Carbon-carbon double bonds Functionalized Horner-Wadsworth-Emmons Reagents Polyunsaturated Aldehydes (+/-)-(E,E)-Coriolic Acid
Kann, Nina
Rein, Tobias
Akermark, Bjoern
Helquist, Paul
The new Horner-Wadsworth-Emmons reagents 4 and 5 transform carbonyl compounds into 2,4-pentadienals and 3-methyl-2,4-pentadienals, respectively.Reagent 4 gives good yields of the desired products with a variety of aldehydes and ketones; reagent 5 generally gives good yields with aldehydes, but gives lower yields with ketones.The reactions proceed under mild conditions and give the products as predominantly 2E,4E isomers, with moderate to good stereoselectivity.In general, pure samples of the 2E,4E-dienals can be obtained after chromatography.Reagents 4 have been used in the key step in a short synthesis of (+/-)-13-hydroxy-9(E),11(E)-octadecanoic acid ((E,E)-coriolic aicd, 45).
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