176979-36-5

Upstream product

• 85710-65-2 (5S)-2,3-Dimethyl-5-isopropenylcyclohex-2-en-1-one 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 6485-40-1 (R)-Carvone 
• 78-39-7 Triethyl orthoacetate 
• 143678-95-9 (1S,5S)-5-Isopropenyl-2,3-dimethylcyclohex-2-en-1-ol 

Downstream Products

• 313653-88-2 1-Diazo-4-((1R,5R)-5-isopropenyl-1,2-dimethyl-cyclohex-2-enyl)-butan-2-one 
• 313653-85-9 3-[(1R,5R)-5-Isopropenyl-1,2-dimethylcyclohex-2-enyl]propionic acid 
• 313653-87-1 (4R,6S)-4-Isopropenyl-6-((E)-3-methoxy-allyl)-1,6-dimethyl-cyclohexene 
• 221664-34-2 (1S,5R)-(5-Isopropenyl-1,2-dimethylcyclohex-2-enyl)acetaldehyde 
• 176979-40-1 1-Diazo-3-((1S,5R)-5-isopropenyl-1,2-dimethyl-cyclohex-2-enyl)-propan-2-one 
• 877856-40-1 (S)-5-Isopropenyl-1-[2-((1R,5R)-5-isopropenyl-1,2-dimethyl-cyclohex-2-enyl)-ethyl]-2,6,6-trimethyl-cyclohex-2-enol 
• 877856-32-1 (3R,5R)-(2-bromoethyl)-5-isopropenyl-2,3-dimethylcyclohexene 
• 176979-39-8 (1S,5R)-5-Isopropenyl-1,2-dimethylcyclohex-2-enylacetic acid 

Relevant academic research and scientific papers

Enantiospecific first total synthesis of ent-Allothapsenol

The enantiospecific first total synthesis of the enantiomer of the irregular sesquiterpene from Ligusticumgrayi allothapsenol, starting from the readily available monoterpene (R)-carvone, is described, which confirmed the assumed absolute configuration of

Enantiospecific synthesis of B-seco-nortaxanes from two molecules of carvone

Enantiospecific syntheses of B-seco-nortaxanes have been accomplished starting from the readily and abundantly available monoterperpene (R)-carvone. Carvone has been converted into both A-ring as well as C-ring derivatives of taxane and coupled with a two

Stereoselective construction of vicinal stereogenic quaternary carbon atoms. Enantiospecific approaches to (+)-valeranef

Two enantiospecific routes to (+)-valerane starting from (R)-carvone, using a combination of Claisen rearrangement and intramolecular diazo ketone cyclopropanation reactions for the stereoselective generation of the vicinal stereogenic quaternary carbon atoms, are described. Thus, orthoester Claisen rearrangement of 3-methylcarveol 6 furnishes the ester 9 containing the first quaternary carbon atom. Intramolecular cyclopropanation of the diazo ketone 10 derived from the ester 9, followed by regioselective reductive cyclopropane cleavage, generates the hydrindanone 11 containing all stereocentres of valerane. Ring expansion of the hydrindanone to tetralone and further reductions transform 11 into (+)-valerane 2. In another direction, homologation of the acid 5 followed by intramolecular cyclopropanation of the diazo ketone 24 and regioselective cyclopropane ring cleavage lead to valerenone 25, which is transformed into (H-)-valerane. The Royal Society of Chemistry 2000.

Stereospecific construction of stereogenic vicinal quaternary carbon atoms. Enantiospecific synthesis of (+)-valerane

Stereo- and enantiospecific synthesis of (+)-valerane starting from R-carvone utilising orthoester Claisen rearrangement and intramolecular diazo ketone cyclopropanation reactions for the construction of the two vicinal quaternary carbon atoms is described.