Chemoenzymatic synthesis of homochiral (R)- and (S)-karahanaenol from (R)-limonene.
Terpinolene oxide, a monoterpene belonging to the p-menthane group, is easily derived from naturally abundant (R)-limonene. It was isomerized with montmorillonite clay catalyst to karahanaenone (2,2, 5-trimethylcyclohept-4-en-1-one) by ring enlargement. The enantiomers of the corresponding alcohol, karahanaenol (2,2, 5-trimethylcyclohept-4-en-1- ol), known for their individual organoleptic properties, were resolved through Pseudomonas cepacia lipase mediated enantiospecific alcoholysis of its acetate derivative.
Roy
A
A
Plantation Products and Flavor Technology Discipline, Central Food Technological Research Institute, Mysore 570 013, India.
D000438:Alcohols / Q000138:chemical synthesis*; D003508:Cycloheptanes / Q000138:chemical synthesis*; D053138:Cyclohexenes; D004798:Enzymes / Q000737:chemistry; D000077222:Limonene; D008049:Lipase / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry*
D000438:Alcohols; D003508:Cycloheptanes; D053138:Cyclohexenes; D004798:Enzymes; D013729:Terpenes; C406251:karahanaenol; D000077222:Limonene; D008049:Lipase