754227-25-3

Upstream product

• 827610-64-0 (1R,5S)-(+)-4,4,6,6-tetramethyl-3-oxabicyclo[3.1.1]heptan-2-one 
• 827610-65-1 (R)-(-)-2,2-dimethyl-3-(1-methylethylidene)cyclobutanecarboxylic acid 
• 827610-63-9 (1R,3S)-(-)-3-(1-hydroxy-1-methylethyl)-2,2-dimethylcyclobutanecarboxylic acid 
• 22571-78-4 (+)-cis-pinononoic acid 
• 827610-66-2 (1S,3R)-3-(1-hydroxy-1-methylethyl)-2,2-dimethylcyclobutanecarboxylic acid 
• 827610-67-3 (1S,5R)-4,4,6,6-tetramethyl-3-oxabicyclo[3.1.1]heptan-2-one 
• 288848-24-8 (1S,3R)-3-acetyl-2,2-dimethylcyclobutane carboxylic acid 
• 827610-68-4 (S)-2,2-dimethyl-3-(1-methylethylidene)cyclobutanecarboxylic acid 

Relevant academic research and scientific papers

Attractant pheromone for the male pink hibiscus mealybug, Maconellicoccus hirsutus (Green) (Homoptera: Pseudococcidae)

A composition for attracting male pink hibiscus mealybugs which contains a carrier material or carrier and effective amount of (R)-lavandulyl (S)-2-methylbutanoate and (R)-maconelliyl (S)-2-methylbutanoate. Also a method for attracting male pink hibiscus mealybugs to an object or area, which method involves treating said object or area with effective amount of (R)-lavandulyl (S)-2-methylbutanoate and (R)-maconelliyl (S)-2-methylbutanoate. Cyclobutanes, 2,2-dimethyl-3-(1-methylethylidene)cyclobutanes, having the formula: wherein R1 is hydrogen, a C1-11 straight or branched alcohol, aldehyde, alkyl, ether (e.g. methanol, ethanal, 4-methylhexane, heptyloxymethane), or esters thereof with a C1-10 saturated or unsaturated, straight or branched acid (e.g., formic acid, acetic acid, 2-methylbutyric acid, 3-methyl-2-butenoic acid) and R2 is hydrogen, methyl, C1-10 saturated or unsaturated, straight or branched alkyl (e.g. hexane, isopropenyl, 4-methyl-4-pentene). A method of disrupting male pink hibiscus mealybug mating with female pink hibiscus mealybugs, involving exposing a pink hibiscus mealybug population to a composition containing a pink hibiscus mealybug mating disrupting effective amount of (R)-lavandulyl (S)-2-methylbutanoate and (R)-maconelliyl (S)-2-methylbutanoate, and optionally a carrier material or carrier.

Enantioselective synthesis of the female sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus

The pink hibiscus mealybug, Maconellicoccus hirsutus (Green), is an exotic insect pest and recently invaded Southern California and Florida. The female M. hirsutus releases the 2-methylbutanoate of a novel cyclobutanoid monoterpene alcohol (maconelliol) that together with lavandulyl 2-methylbutanoate constitutes the sex pheromone to attract males from a distance. Enantioselective syntheses of four different stereoisomers of the major component, maconelliyl 2-methylbutanoate 1, from α-pinene are reported. Absolute configurations of both naturally occurring maconelliyl 2-methylbutanoate 1 and the minor component, lavandulyl 2-methylbutanoate 2, have been established. Comparison of the analytical data of naturally occurring compounds with those of optically active synthetic isomers proved that both esters show the (R)-configuration at the alcohol and the (S)-configuration at acid moieties.

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.