N. Plobeck, J. Baeckvall
Jul 1, 1991
Citations
0
Influential Citations
29
Citations
Journal
Journal of Organic Chemistry
Abstract
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 benzenesulfonic 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