Journal of Organic Chemistry p. 4508 - 4512 (1991)
Update date:2022-08-05
Topics:
Plobeck, Niklas A.
Baeckvall, Jan-E.
A procedure for the preparation of 2E,4E unsaturated carboxylic acid derivatives from dienes was developed.Transformation of terminal 1,3-dienes to (E)-2-phenylsulfonyl 1,3-dienes and subsequent addition of a carboxy anion equivalent and elimination of benzenesulfinic acid led to 2,4-dienoic amides and esters.In this way the natural products N-isobutyl-2(E),4(E)-undecadienamide (1a), N-isobutyl-2(E),4(E)-decadienamide (pellitorine, 1b), and methyl 2(E),4(E)-decadienoate (1c) were obtained in high isomeric purity.
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