Submitted to: Tetrahedron Letters
Publication Type: Peer reviewed journal
Publication Acceptance Date: 10/27/2004
Publication Date: 4/1/2005
Citation: Zhang, A., Nie, J., Khrimian, A. 2005. Chiral synthesis of maconelliol: a novel cyclobutanoid terpene alcohol from pink hibiscus mealybug, maconellicoccus hirsutus.. Tetrahedron Letters. 45:9401-9403. Interpretive Summary: The pink hibiscus mealybug (PHM) is sap-sucking invasive species, which attacks many agricultural crops, vegetable crops, forest trees, and ornamental plants. As it feeds, PHM injects toxic saliva into the plant that results in malformed leaf and shoot growth, stunting, and occasional plant death. Potential losses of $750 million per year have been estimated if the insect cannot be controlled. Early attempts to control PHM using pesticides failed because they are covered with a protected wax secretion that prevents pesticide penetration. Classical biological control is successful against PHM; however, these programs have been hindered by the lack of an easy method for detecting mealybug presence and spread. One way to do that is by isolating sex attractant from female insects and use it to attract males. We have successfully synthesized the right forms of sex attractant components. Traps baited with this right form of sex attractant have been used by APHIS as an economical, convenient, and useful survey tool for PHM population monitoring in Florida in 2004. In addition, the attractant will enable the future development of mass trapping, attract-and-kill, and mating disruption technologies for growers to manage this pest.
Technical Abstract: The Chiral synthesis of maconelliol, [2,2-dimethyl-3-(1-methylethylidene)cyclobutyl] methanol, the alcohol moiety of the major sex pheromone component isolated from the pink hibiscus mealybug, Maconellicoccus hirsutus, is described. The compound was synthesized in 6 steps from alpha pinene and key step is dehydration of 5 to 7 through the intermediate 6. The absolute configuration of the naturally occurring maconelliol was confirmed as R.