Efficient synthesis of (+/-)-4-methyloctanoic acid, aggregation pheromone of rhinoceros beetles of the genus Oryctes (Coleoptera: Dynastidae, Scarabaeidae).
(+/-)-4-Methyloctanoic acid and its ethyl ester are aggregation pheromones of many rhinoceros beetles of the genus Oryctes and are investigated for the control of these pests by olfactory trapping. A simple, economical, and high-yield (>50%) synthesis of (+/-)-4-methyloctanoic acid and its ethyl ester is presented starting from n-hexanal. The key step in this sequence is an orthoester Claisen rearrangement for the elongation of the carbon chain by two.
Ragoussis
Valentine
V
Department of Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis Zographou, Athens, Greece. ragousi@chem.uoa.gr
Giannikopoulos
Alexandros
A
Skoka
Efthymia
E
Grivas
Panagiotis
P
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D002210:Caprylates / Q000138:chemical synthesis*; D001517:Coleoptera; D010675:Pheromones / Q000138:chemical synthesis*
D000447:Aldehydes; D002210:Caprylates; D010675:Pheromones; C521814:4-methyloctanoic acid; C103470:ethyl 4-methyloctanoate; C010463:n-hexanal