Insect repellent analogs of dihydronepetalactone

ORGN 527

Mark A. Scialdone and Ann Y. Liauw. DuPont Central Research & Development, P.O. Box 80328 Experimental Station, Wilmington, DE 19880-0328
The naturally occurring iridoid monoterpene nepetalactone and its reduced form dihydronepetalactone (DHN) have demonstrated insect repellency. Nepetalactone can be viewed as an unsaturated bicyclic lactone derived from an intramolecular dehydration of a (cyclopentylmethyl)-aldehyde-carboxylate, namely nepetalic acid. Nepetalic acid derived from hydration of cis,trans-nepetalactone affords a single diastereomer by crystallization.

Addition of Grignard reagents to nepetalic acid results in carbon-carbon bond formation at the acetal carbon to afford substituted DHN analogs. The degree of diastereoselectivity of this addition and mosquito repellency of these DHN analogs will be presented.

 

Practical Synthesis and Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- 201B, Oral

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004