Submitted to: Synthetic Communications
Publication Type: Peer reviewed journal
Publication Acceptance Date: 6/29/2004
Publication Date: 12/1/2004
Citation: Shirali, S., Zhang, A. 2004. Enantioselective synthesis of (r)-2-methyl alkanoic acids: a convenient approach to a-substituted chiral carboxylic acid derivastives.. Synthetic Communications. 34:3435-3441. Interpretive Summary: The pink hibiscus mealybug (PHM) causes severe economic problems throughout the world. This exotic insect pest has been spreading through the entire Caribbean region since it was first detected on the island of Grenada in 1994. Since then, it has spread to Southern California, Mexico, and Central America. Agricultural crops in the United States expected to be at greatest economic risk to PHM invasion include ornamental crops, vegetable crops, citrus, grapes, and avocados. Potential losses of $750 million per year have been estimated if the insect cannot be controlled. Females of the PHM produce a sex attractant (pheromone) that consists of two chemical compounds, each of which exists in different conformations. During the identification process, we found a method that could be used to prepare precursors useful in making all conformations of the pheromone compounds. This method was used to conveniently synthesize the attractants. The synthetic pheromone provides an economical, convenient, and useful tool for PHM population monitoring. Sex attractant-baited traps will be useful in the study of the seasonal life history of PHM. It should also enable the development of mass trapping and mating disruption technology for growers to manage this pest, and it might complement biological control eradication programs, such as that currently underway in the Caribbean.
Technical Abstract: Racemization-free deacylation of N-acylated-imidazolidine-2-one derivatives affords corresponding a-substituted chiral carboxylic acids in high yield along with recovery of the chiral auxiliary using lithium hydroperoxide.