Efficient Synthesis of (±)-4-Methyloctanoic Acid, Aggregation Pheromone of Rhinoceros Beetles of the Genus Oryctes (Coleoptera:  Dynastidae, Scarabaeidae)

Valentine Ragoussis,* Alexandros Giannikopoulos, Efthymia Skoka, and Panagiotis Grivas
Department of Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis Zographou, 15771 Athens, Greece
J. Agric. Food Chem., 2007, 55 (13), pp 5050–5052
DOI: 10.1021/jf0704662
Publication Date (Web): May 27, 2007
Copyright © 2007 American Chemical Society
*

 Corresponding author (telephone + 30 210 7274497; fax + 30 210 7274761; e-mail ragousi@chem.uoa.gr).

Abstract

Abstract Image

(±)-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.

Keywords: Pheromone synthesis; rhinoceros beetles; Oryctes elegans; Oryctes rhinoceros; Oryctes monoceros; 4-methyloctanoic acid; ethyl-4-methyloctanoate; Claisen rearrangement

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History

  • Published In Issue June 27, 2007
  • Received for review February 16, 2007. Revised manuscript received April 10, 2007. Accepted April 11, 2007. The work has been in part supported by a grant from the Special Account for Research Grants of the University of Athens, Greece.

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