| Title: | "New syntheses of 1,7-dimethylnonyl propanoate, the western corn rootworm pheromone, in four different ways via cross metathesis, alkylation and coupling reactions" |
| Address: | "Photosensitive Materials Research Center, Toyo Gosei Co., Ltd., Inba-gun, Chiba, Japan. kjk-mori@arion.ocn.ne.jp" |
| Journal Title: | Biosci Biotechnol Biochem |
| ISSN/ISBN: | 1347-6947 (Electronic) 0916-8451 (Linking) |
| Abstract: | "A mixture of the four stereoisomers of 1,7-dimethylnonyl propanoate, the female sex pheromone of the western corn rootworm (Diabrotica virgifera virgifera LeConte), was synthesized in four different ways by employing one of the following four reactions as the key step: (i) cross metathesis using the Grubbs I catalyst, (ii) cross metathesis using the Grubbs II catalyst, (iii) alkylation of an alkynide anion, and (iv) Grignard coupling in the presence of dilithium tetrachlorocuprate. Although the cross metathesis approaches enabled two short syntheses (4 or 6 steps) of the pheromone to be achieved, the cheapest and most efficient synthesis was possible via Grignard coupling to give the desired pheromone in a 40% overall yield based on 2-methyl-1-butanol (8 steps)" |
| Keywords: | 1-Butanol/chemistry Alkylation Animals Chlorides/chemistry Coleoptera/*metabolism Copper/chemistry Female Pentanols/chemistry Propionates/*chemical synthesis Sex Attractants/*chemical synthesis; |
| Notes: | "MedlineMori, Kenji eng England 2010/03/09 Biosci Biotechnol Biochem. 2010; 74(3):595-600. doi: 10.1271/bbb.90805. Epub 2010 Mar 7" |
