175779-08-5

Upstream product

• 6485-40-1 (R)-Carvone 
• 113405-31-5 (2S,3R,5R)-2-allyl-2,3-dimethyl-5-isopropenyl-cyclohexan-1-one 

Downstream Products

• 214215-76-6 Acetic acid (1R,3R,4S)-3,4-dimethyl-5-oxo-4-(2-oxo-propyl)-cyclohexyl ester 
• 214215-78-8 (-)-(5R,6S)-5,6-dimethyl-6-(2-oxopropyl)cyclohex-2-enone 
• 39900-30-6 (-)-(2S,3R)-2,3-dimethyl-2-(2-oxopropyl)cyclohexanone 

Relevant academic research and scientific papers

Chiral synthons from carvone. Part 50. Enantiospecific approaches to both enantiomers of bicyclo[4.3.0]nonane-3,8-dione derivatives

Enantiospecific synthesis of both enantiomeric forms of bicyclo[4.3.0]nonane-3,8-dione derivatives has been described starting from (R)-carvone employing two different cyclopentannulation methodologies. Thus, in the first methodology, carveol (5) was converted into tricyclic ketone 4 employing a Claisen rearrangement and intramolecular diazo ketone cyclopropanation reactions. Degradation of the isopropenyl group followed by cyclopropane cleavage and cuprate addition generated the dione (-)-12a. Whereas, a Wacker mediated cyclopentannulation of (R)-carvone via the dione 15 furnished the, enone 17. Functional group manipulation including the degradation of isopropenyl group transformed the enone 17 into the dione (+)-12a, which on regioselective ketalisation generated the ketoketal (+)-2.

Enantiospecific synthesis of (+)-(1S,2R,6S)-1,2- dimethylbicyclo[4.3.0]nonan-8-one and (-)-7-epibakkenolide-A

Synthesis of the chiral bicyclic ketone mentioned in the title starting from R-carvone, and its elaboration to 7-epibakkenolide-A is described. Conjugate addition of dimethyl copperlithium to R-carvone followed by alkylation of the intermediate enolate generated the allylated compound 6, which was transformed into the diketone 12 via a sequence of reactions comprising regiospecific Wacker oxidation, ozonation-Criegee rearrangement as key reactions. Intramolecular aldol condensation followed by catalytic hydrogenation converted the diketone 12 into the bicyclic ketone (+)-3, the optical antipode of the compound derived from the sesquiterpenes bakkenolide- A and fukinone. A 5-exo-dig radical cyclisation based strategy transformed the bicyclic ketone 3 into chiral 7-epibakkenolide-A.

Enantioselective synthesis of both (+)-and (-)-derivatives of bicyclo[4.3.0]nonan-8-one and -3,8-diones from R-carvone 1

Enantioselective synthesis of both the enantiomeric forms of the hydrindane derivatives mentioned in the title, potential chiral precursors in terpenoid synthesis, starting from R-carvone employing two different cyclopentannulation methodologies is described.