22571-78-4

Upstream product

• 18309-32-5 Verbenone 
• 80-56-8 rac-α-pinene 
• 80-57-9 (+)-verbenone 
• 132478-08-1 cis-pinononic aldehyde 
• 1820-09-3 Verbenol 
• 4755-33-3 pinane 
• 64-19-7 acetic acid 
• 80-56-8 Pinene 
• 7732-18-5 water 
• 10028-15-6 ozone 
• 20536-50-9 (-)-(1S,2S,5S)-2-hydroxy-pinan-3-one 
• 22339-08-8 (+)-trans-verbenol 
• 28587-41-9 cis-3-acetyl-2,2-dimethylcyclobutylmethanoic acid 
• 80-57-9 (-)-Verbenone 

Downstream Products

• 473-68-7 (-)-trans-pinononoic acid 
• 21660-24-2 ((1S)-2.2-dimethyl-3c-acetohydroximoyl-cyclobutyl-(r))-acetic acid 
• 77370-41-3 3-methylbutane-1,2,3-tricarboxylic acid 
• 754227-26-4 (R)-(-)-[2,2-dimethyl-3-(1-methylethylidene)cyclobytyl] methanol 
• 754227-25-3 (S)-(+)-maconelliol 
• 1616704-81-4 (1S,3R)-2,2-dimethyl-3-((((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)carbonyl)cyclobutane-1-carboxylic acid 
• 1616705-33-9 1-benzyl 3-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl) (1S,3R)-2,2-dimethylcyclobutane-1,3-dicarboxylate 
• 1616705-62-4 (1R,3S)-3-((benzyloxy)carbonyl)-2,2-dimethylcyclobutane-1-carboxylic acid 
• 1616705-61-3 1-benzyl 3-(tert-butyl) (1S,3R)-2,2-dimethylcyclobutane-1,3-dicarboxylate 
• 177316-73-3 1-((1S)-2,2,3c-trimethyl-cyclobut-r-yl)-ethanone 
• 188918-50-5 (1S,3R)-3-[(tert-butoxycarbonyl)amino]-2,2-dimethylcyclobutane-1-carboxylic acid 
• 188918-42-5 (1S,3R)-3-((benzyloxy)carbonyl)-2,2-dimethylcyclobutane-1-carboxylic acid 
• 527751-18-4 (1S,3R)-3-amino-2,2-dimethylcyclobutan-1-carboxylic acid 
• 28465-10-3 (+)-(1R)-cis-2,2-dimethyl-3-isopropenylcyclobutanemethanol acetate 

Relevant academic research and scientific papers

Ozonolysis of verbenone in aprotic solvents

The ozonolysis of verbenone in methylene chloride and acetonitrile at -60 and 0 °C proceeds with cleavage of the double bond and neighbouring σ-bond to give (1R,3S)-acetyl-2,2-dimethylcyclobutane carboxylic acid. The mechanism of the reaction has been pro

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.

NOVEL BETULINIC ACID PROLINE DERIVATIVES AS HIV INHIBITORS

The invention relates to novel betulinic acid derivatives and related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases. These compounds are esterified in position 3 and are substituted in position 17 of the betulinic acid structure, via a linking group W, by a saturated 5-7 membered nitrogen-heterocycle.

AMINOPYRIMIDINES AS SYK INHIBITORS

The present invention provides novel pyrimidine amines of formula I which are potent inhibitors of spleen tyrosine kinase, and are useful in the treatment and prevention of diseases mediated by said enzyme, such as asthma, COPD, rheumatoid arthritis and cancer.

Ozonolysis of verbenone in methanol

The conditions of ozonolysis of verbenone in methanol strongly affect the mechanism of formation of the major product, (1R,3S)-3-acetyl-2,2- dimethylcyclobutane-1-carboxylic acid.

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.

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.

Chiral 1,3-cyclobutane amino acids: Syntheses and extended conformations

Optically active samples of the N-protected 1,3-cyclobutane amino acids 1 and 2 were prepared from α-pinene. The synthesis of 1 is enantiodivergent insofar as both optical antipodes of the product can be prepared from the same α-pinene enantiomer. Single crystal X-ray diffraction studies of derivatives of 1 reveal these compounds can have extended conformations.

Radical chemistry based on (+)-cis-pinononic and (+)-cis-pinonic acids

A high yield method for the preparation of (+)-cis-pinononic acid starting from the inexpensive (+)-α-pinene has been developed. The capture of the cyclobutyl radical from decarboxylation of (+)-cis-pinonic acid has been investigated. Moreover the radical