Spilantholの合成研究 (第4報)

Isospilanthol (N-イソブチル-4,6-デカジエンアマイド) の合成

抄録

Ethyl 6-hydroxy-4-decaenoate, obtained by the Grignard condensation of ethyl 5-formyl-4-pentenoate and butyl iodide, was converted to the methyl ester, dehydrated to methyl 4, 6-decadienoate, and reacted with isobutylamine to 4, 6-decadienoic acid isobutylamide as colorless needles, m.p. 53°. This amide is a solid and only gives a mild but persistent paralytic action on the tongue, without any acrid taste, while the natural spilanthol is a liquid of b. p_0·015 138°, possessing an acrid taste and a persistent paralytic action. From these facts, it is assumed that the two are geometric isomers.