SYNTHESIS OF (Z)-14-HEPTADECEN-4-OLIDE AND (Z)-11-PENTADECEN-4-OLIDE,SEX-PHEROMONE ANALOGS OF OSTRINIA-NUBILALIS AND CYDIA-MOLESTA

Authors
HOSKOVEC M SAMAN D KOUTEK B
Citation
M. Hoskovec et al., SYNTHESIS OF (Z)-14-HEPTADECEN-4-OLIDE AND (Z)-11-PENTADECEN-4-OLIDE,SEX-PHEROMONE ANALOGS OF OSTRINIA-NUBILALIS AND CYDIA-MOLESTA, Collection of Czechoslovak Chemical Communications, 59(5), 1994, pp. 1211-1218
Citations number
15
Categorie Soggetti
Chemistry
Journal title
Collection of Czechoslovak Chemical Communications → ACNP
ISSN journal
00100765
Volume
59
Issue
5
Year of publication
1994
Pages
1211 - 1218
Database
ISI
SICI code
0010-0765(1994)59:5<1211:SO(A(>2.0.ZU;2-G
Abstract
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 O strinia nubilalis and Cydia molesta, was efficient cross-coupling reac tion of 3-methoxycarbonylpropanoyl chloride with corresponding (Z)-alk enylmagnesium bromides. The methyl 4-oxo-(Z)-14-heptadecenoate (Va) an d methyl 4-oxo-(Z)-11-pentadecenoate (Vb) prepared in this way were co nverted by one-pot reaction using sodium borohydride in an ethanolic s olution to the required (Z)-alken-4-olides (VIa,VIb).