Chiral synthesis of maconelliol: a novel cyclobutanoid terpene alcohol from pink hibiscus mealybug, Maconellicoccus hirsutus

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 six steps from alpha-pinene and the key step is dehydration of 5 to 7 through the intermediate 6. The absolute configuration of the naturally occurring maconelliol was determined as R.