Facile synthesis of Iridomyrmecin diastereomers from catnip oil component nepetalactone

Authors: Chauhan, Kamlesh; Schmidt, Walter

Submitted to: Tetrahedron Letters
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 3/5/2014
Publication Date: 3/25/2014
Citation: Chauhan, K.R., Schmidt, W.F. 2014. Facile synthesis of Iridomyrmecin diastereomers from catnip oil component nepetalactone. Tetrahedron Letters. 55(1):2534-2536.

Interpretive Summary: Pressing public health problems involving serious diseases such as malaria, dengue, and yellow fever, require repellants and controls of the blood-sucking insect vectors. Using natural compounds of the plant in the mint family known as catnip, we have produced certain volatile chemicals (nepetalactones). These chemicals could be important building blocks for the synthesis of biopesticide and insect repellents. We have developed a simple synthetic method to obtain defensive compounds of insect origin in large quantities by utilizing catnip oil. Efficient sythesis and easy availability of these compounds is proving very useful in the development of public health pesticides against blood sucking insects which are disease vectors. This is of use to scientists and pest management companies using natural products as renewable sources, to combat insect-vectored threats to human health.

Technical Abstract: Iridomyrmecin and analogues have been synthesized in 3 steps from 4aS,7S,7aR and 4aS,7S,7aR-nepetalactones, major components of catnip oil. Iridomyrmecin is an indigenous to plants and insects and availability of its diastereomers in enantiomerically pure form is being very useful in the evaluation of user friendly arthropod pest control candidates.