Collect. Czech. Chem. Commun. 1994, 59, 1211-1218

Synthesis of (Z)-14-Heptadecen-4-olide and (Z)-11-Pentadecen-4-olide, Sex Pheromone Analogues of Ostrinia nubilalis and Cydia molesta

Michal Hoskovec, David Šaman and Bohumír Koutek

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


The key step in the preparation of racemic (Z)-14-heptadecen-4-olide (VIa) and (Z)-11-pentadecen-4-olide (VIb), sex pheromone analogues of Ostrinia nubilalis and Cydia molesta, was efficient cross-coupling reaction of 3-methoxycarbonylpropanoyl chloride with corresponding (Z)-alkenylmagnesium bromides. The methyl 4-oxo-(Z)-14-heptadecenoate (Va) and methyl 4-oxo-(Z)-11-pentadecenoate (Vb) prepared in this way were converted by one-pot reaction using sodium borohydride in an ethanolic solution to the required (Z)-alken-4-olides (VIa, VIb).