Submitted to: American Chemical Society Abstracts
Publication Type: Abstract only
Publication Acceptance Date: 3/28/2007
Publication Date: 8/19/2007
Citation: Petroski, R.J., Bartelt, R.J. 2007. Synthesis of a dimethylfuran-containing macrolide insect pheromone [abstract]. American Chemical Society Abstracts. Paper No. 179. Interpretive Summary:
Technical Abstract: Grignard chemistry was utilized to construct a key trisubstituted furan intermediate (3,4-dimethyl-2-[5-(tetrahydroppyran-2-yloxy)pentyl]furan) from 2,3-dimethylbutenolide, prepared via a Reformatsky route. The carbon skeleton of the macrolide pheromone also requires construction of a propionic acid side chain, which was previously done in four steps: formylation, Horner-Wadsworth-Emmons olefination, reduction of the unsaturated ester double bond, and soponification. The use of various three-carbon homologating agents for the direct construction of the propionic acid side chain will be discussed. The remaining steps of THP deprotection and closure of the lactone ring were straightforward. The pheromone can be used to monitor populations of insects, Galerucella calmariensis and Galerucella pusilla (Coleoptera: Chrysomelidae) that have been introduced into North America as biological control agents for the invasive wetland weed purple loosestrife, Lythrum salicaria.