Synthesis of the pheromone of the longtailed mealybug, a sterically congested, irregular monoterpenoid.
A straightforward and scaleable synthesis of the sterically congested pheromone of the longtailed mealybug, with two adjacent quarternary carbons in a cyclopentene ring, was accomplished in 13.5% overall yield. Key steps included regiospecific cyclization of an alpha-diazo-beta-ketoester to build the cyclopentane ring, followed by reduction of the enol triflate of the ketone to place the double bond.
Zou
Yunfan
Y
Department of Entomology, University of California, Riverside, California 92521-0001, USA.
Millar
Jocelyn G
JG
D000818:Animals; D001391:Azo Compounds / Q000737:chemistry; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D006430:Hemiptera / Q000737:chemistry* / Q000502:physiology; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry
D001391:Azo Compounds; D003517:Cyclopentanes; D004952:Esters; D007659:Ketones; D039821:Monoterpenes; D010675:Pheromones; D012724:Sex Attractants