28465-10-3

Upstream product

• 473-66-5 cis-(-)-verbanone 
• 18358-54-8 cis-(-)-2,2-dimethyl-3-(1-methylethenyl)cyclobutanal 
• 28465-11-4 (1R-cis)-(+)-2,2-dimethyl-3-isopropenyl-cyclobutane carboxylic acid 
• 39863-91-7 trans-(R)-verbenol acetate 
• 22339-08-8 (+)-trans-verbenol 
• 7785-70-8 (+)-α-pinene 
• 177316-71-1 (1R,3S)-(+)-cis-3-acetyl-1-(2-acetoxyethenyl)-2,2-dimethylcyclobutane 
• 93921-54-1 (1R,3S)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylic acid methyl ester 
• 28465-12-5 (1R,3S)-3-isopropenyl-2,2-dimethylcyclobutanecarboxylic acid methyl ester 
• 22571-78-4 (+)-cis-pinononoic acid 
• 71628-89-2 (1S,3S)-3-acetyl-2,2-dimethylcyclobutaneacetaldehyde1,6-cyclodecanedione 
• 675605-82-0 (S)-2-[(1S,3R)-3-hydroxymethyl-2,2-dimethylcyclobutyl]-1,2-propanediol 
• 108-24-7 acetic anhydride 
• 149-73-5 trimethyl orthoformate 

Relevant academic research and scientific papers

ISOLATION, IDENTIFICATION AND SYNTHESIS OF THE SEX PHEROMONE OF THE CITRUS MEALYBUG, PLANOCOCCUS CITRI (RISSO)

The sex attractant pheromone of the citrus mealybug, Planococcus citri (Risso), has been identified as (1R-cis)-(+)-2,2-dimethyl-3-(1-methylethenyl)cyclobutanemethanol acetate (VI).

Novel synthesis of Planococcus citri pheromone

An effective method was proposed for synthesizing (+)-cis-1R-acetoxymethyl- 3-isopropenyl-2,2-dimethylcyclobutane, a pheromone of the citrus mealybug, based on ozonolysis of verbenone that led in one step to the key synthon 1R,3S-3-acetyl-2,2-dimethylcyclobutanecarboxylic acid. 2006 Springer Science+Business Media, Inc.

Synthesis of the Female Sex Pheromone of the Citrus Mealybug, Planococcus citri

The citrus mealybug, Planococcus citri (Risso) is a common pest in the Southern U. S. and the Mediterranean. Two alternative syntheses of the female sex pheromone, (1R)-(+)-cis-2,2-dimethyl-3-isopropenyl-cyclobutane methanol acetate, have been developed. Key transformations include an allylic oxidation of (1R)-(+)-α-pinene to (+)-R-verbenone, oxidative decarboxylation using RuCl3-NalO4, and methylenation with Zn/CH 2Br2/TiCl4.

Synthesis of the sex pheromone of the citrus mealybug, Pseudococcus cryptus

The sex pheromone of the citrus mealybug (Pseudococcus cryptus), [(1R,3R)-3-isopropenyl-2,2-dimethylcyclobutyl]methyl 3-methyl-3-butenoate, was synthesized from (+)-α-pinene in five operational steps in a 43% overall yield. The synthetic pheromone was identical with the natural pheromone in 1H-NMR and mass spectroscopic properties, and showed almost the same pheromonal activity as the natural pheromone.

OZONOLYSIS OF ALKENES AND THE REACTIONS OF POLYFUNCTIONAL COMPOUNDS XLIII. SYNTHESIS OF (1R,3R)-(+)-CIS-1-ACETOXYMETHYL-3-ISOPROPENYL-2,2-DIMETHYLCYCLOBUTANE - THE SEX PHEROMONE OF THE VINE MEALY BUG (PLANOCOCCUS CITRI) AND ITS (1S,3S)-(-)-CIS-ENANTIOMER

(1R,3R)-(+)-cis-1-Acetoxymethyl-3-isopropenyl-2,2-dimethylcyclobutane, which is the sex pheromone of the vine mealy bug (Planococcus citri), and its (1S,3S)-(-)-cis-enantiomer were synthesized from (+)- or (-)-α-pinene by ozonolysis in two stages.The overall yield of the required compounds calculated on the initial α-pinenes amounted to about 40percent.

Synthesis of the Female Sex Pheromone of the Citrus Mealybug, Planoccus citri (Risso)

The synthesis of (1R-cis)-(+)-2,2-dimethyl-3-isopropenylcyclobutanemethanol acetate, 1, a female sex pheromone of the Citrus Mealybug, Planoccus citri (Risso), is described.Ruthenium catalyzed oxidative decarboxylation of (+)-verbenone or (+)-verbenol yields (+)-pinononic acid, 4, which was further elaborated in a Wittig step, reduced with lithium aluminium hydride and subsequently acylated to yield 1.