Enantioselective synthesis of(S)-3,7-dimethyl-2-oxo-6-octene-1,3-diol, a Colorado potato beetle (CPB)pheromone

Authors: BATHINI, NAGENDRA - HMJ FNDTN, ROCKVILLE,MD; CHAUHAN, KAMLESH

Submitted to: Tetrahedron Letters
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 10/15/2008
Publication Date: 10/20/2008
Citation: Bathini, N.B., Chauhan, K.R. 2008. Enantioselective synthesis of(S)-3,7-dimethyl-2-oxo-6-octene-1,3-diol, a Colorado potato beetle (CPB)pheromone. Tetrahedron Letters. 50:66-67.

Interpretive Summary: Colorado potato beetle (CPB) is the most important agriculture pest, affecting billions of dollars of crops of potato worldwide. At present there are limited alternatives to control this pest other than synthetic pesticides, to which CPB has repeatedly become resistant. An alternative method is needed to synthetically produce the chemicals (pheromones) that Colorado potato beetles make to attract other beetles. The synthetic pheromone can be used to attract CPB and kill them. We developed a low-cost method to produce this pheromone. It will lead to products (insect attractants) to control the beetle and will be useful for farmers and professional practicing integrated pest management.

Technical Abstract: Chiral semiochemicals are difficult to synthesize by conventional approach. However when plant based natural products are identified as chiral synthones, synthesis of such complex semiochemicals become facile and commercially viable. This report concerns identification of natural source namely mannitol. We used mannitol as chiral synthone to produce (S)-3,7-dimethyl-2-oxo-6-octene-1,3-diol, a CPB pheromone in multigram quantity.