A VERSATILE APPROACH TO THE SYNTHESIS OF 9(Z)-UNSATURATED ACYCLIC INSECT PHEROMONES FROM UNDEC-10-ENOIC ACID

Authors
ISHMURATOV GY KHARISOV RY YAKOVLEVA MP BOTSMAN OV GALEEVA RI ISHMURATOVA NM TOLSTIKOV GA
Citation
Gy. Ishmuratov et al., A VERSATILE APPROACH TO THE SYNTHESIS OF 9(Z)-UNSATURATED ACYCLIC INSECT PHEROMONES FROM UNDEC-10-ENOIC ACID, Russian chemical bulletin, 47(8), 1998, pp. 1595-1597
Citations number
13
Categorie Soggetti
Chemistry
Journal title
Russian chemical bulletin → ACNP
ISSN journal
10665285
Volume
47
Issue
8
Year of publication
1998
Pages
1595 - 1597
Database
ISI
SICI code
1066-5285(1998)47:8<1595:AVATTS>2.0.ZU;2-Y
Abstract
A general approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid was developed. The method compris es the conversion of the acid into undec-10-enyl acetate, shortening o f its carbon chain to afford dec-9-enyl acetate (via 11-acetoxyundecan oic acid), and a two-step transformation of the latter into the key in termediate, dec-9-yn-l-ol, by sequential bromination-dehydrobrominatio n. The elimination of two HBr molecules from the dibromide is effectiv ely performed using (BuOK)-O-t in the presence of dibenzo-18-crown-6 a s the catalyst.