175695-67-7

Upstream product

• 167611-58-7 (1R,5R)-ethyl <(2-methyl-5-isopropenyl)-cyclohex-2-ene>-1-acetate 
• 147397-89-5 2-methyl-5-isopropenyl-2-cyclohexen-1-acetic acid 
• 6485-40-1 (R)-Carvone 
• 204526-19-2 (+)-(1R,5R)-5-Isopropenyl-2-methylcyclohex-2-enylacetic acid 
• 99-48-9 (4R,6R)-carveol 
• 186581-53-3 diazomethane 

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.

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.