85710-65-2

Upstream product

• 85710-64-1 1,2-dimethyl-5-(1-methylethenyl)cyclohex-2-en-1-ol 
• 127841-75-2 (R)-5-Isopropenyl-7a-methyl-3,3a,4,5,6,7a-hexahydro-indazol-7-one 
• 186581-53-3 diazomethane 
• 6485-40-1 (R)-Carvone 
• 852930-25-7 (R)-2-methylcarveol 
• 75-16-1 methylmagnesium bromide 
• 917-64-6 methyl magnesium iodide 
• 143612-00-4 (-)-(1S,4S,6S)-4-isopropenyl-1,6-dimethyl-7-oxabicyclo[4.1.0]heptan-2-one 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 127911-96-0 (1R,5R)-5-Isopropenyl-1,2-dimethyl-cyclohex-2-enol 

Downstream Products

• 85710-67-4 (5R)-5-(1-Chloro-1-methylethyl)-2,3-dimethylcyclohex-2-en-1-one 
• 443747-86-2 (3S,5R)-2-Allyl-5-isopropenyl-2,3-dimethyl-cyclohexanone 
• 172588-01-1 (2R,3S,5R)-5-Isopropenyl-2,3-dimethyl-2-(2-oxo-propyl)-cyclohexanone 
• 14087-71-9 (-)-cis-dihydrochrysanthemolactone 
• 85710-68-5 (5S)-5-(1-Chloro-1-methylethyl)-2,3-dimethylcyclohex-2-en-1-one 
• 159527-68-1 (+)-(S)-2,3-dimethyl-5-(2-bromoprop-2-yl)-cyclohex-2-en-1-one 
• 143678-95-9 (1S,5S)-5-Isopropenyl-2,3-dimethylcyclohex-2-en-1-ol 
• 877856-32-1 (3R,5R)-(2-bromoethyl)-5-isopropenyl-2,3-dimethylcyclohexene 
• 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 
• 176979-36-5 (-)-(3R,5R)-5-isopropenyl-1,2-dimetylcyclohex-2-ene-1-acetic acid ethyl ester 
• 328934-89-0 (-)-(3R,5R)-3-(2-hydroxyethyl)-5-isopropenyl-2,3-dimethylcyclohexane 
• 868387-84-2 (-)-(2S,4S)-2-acetyl-4-isopropenyl-2-methylcyclopentanone 
• 176979-40-1 1-Diazo-3-((1S,5R)-5-isopropenyl-1,2-dimethyl-cyclohex-2-enyl)-propan-2-one 
• 221664-34-2 (1S,5R)-(5-Isopropenyl-1,2-dimethylcyclohex-2-enyl)acetaldehyde 

Relevant academic research and scientific papers

A stereoselective total synthesis of (-)-seychellene

A stereoselective total synthesis of the tricyclic sesquiterpene (-)-seychellene, starting from (R)-carvone via (R)-3-methylcarvone has been accomplished, employing a combination of intermolecular Michael addition-intramolecular Michael addition sequence,

The first enantiospecific total synthesis of (+)-seychellene

The first enantiospecific total synthesis of the tricyclic sesquiterpene (+)-seychellene, starting from (R)-carvone via (S)-3-methylcarvone, has been accomplished employing a combination of an intermolecular Michael addition-intramolecular Michael additio

C3 and C6 Modification-Specific OYE Biotransformations of Synthetic Carvones and Sequential BVMO Chemoenzymatic Synthesis of Chiral Caprolactones

The scope for biocatalytic modification of non-native carvone derivatives for speciality intermediates has hitherto been limited. Additionally, caprolactones are important feedstocks with diverse applications in the polymer industry and new non-native terpenone-derived biocatalytic caprolactone syntheses are thus of potential value for industrial biocatalytic materials applications. Biocatalytic reduction of synthetic analogues of R-(?)-carvone with additional substituents at C3 or C6, or both C3 and C6, using three types of OYEs (OYE2, PETNR and OYE3) shows significant impact of both regio-substitution and the substrate diastereomer. Bioreduction of (?)-carvone derivatives substituted with a Me and/or OH group at C6 is highly dependent on the diastereomer of the substrate. Derivatives bearing C6 substituents larger than methyl moieties are not substrates. Computer docking studies of PETNR with both (6S)-Me and (6R)-Me substituted (?)-carvone provides a model consistent with the outcomes of bioconversion. The products of bioreduction were efficiently biotransformed by the Baeyer–Villiger monooxygenase (BVase) CHMO_Phi1 to afford novel trisubstituted lactones with complete regioselectivity to provide a new biocatalytic entry to these chiral caprolactones. This provides both new non-native polymerization feedstock chemicals, but also with enhanced efficiency and selectivity over native (+)-dihydrocarvone Baeyer–Villigerase expansion. Optimum enzymatic reactions were scaled up to 60–100 mg, demonstrating the utility for preparative biocatalytic synthesis of both new synthetic scaffold-modified dihydrocarvones and efficient biocatalytic entry to new chiral caprolactones, which are potential single-isomer chiral polymer feedstocks.

Novel PDC catalyzed oxidative rearrangement of tertiary allylic alcohols to β-substituted enones

Novel pyridinium dichromate (PDC) catalyzed oxidative rearrangement for the conversion of tertiary allylic alcohols to ?-substituted enones is described. Using a catalytic amount of PDC with PhI(OAc)2 as a co-oxidant in the presence of magnesium sulfate and water under oxygen was found effective for this rearrangement.

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

Lewis acid-catalyzed oxidative rearrangement of tertiary allylic alcohols mediated by TEMPO

Two methods for the oxidative rearrangement of tertiary allylic alcohols have been developed. Most of tertiary allylic alcohols studied were oxidized to their corresponding transposed carbonyl derivatives in excellent to fair yields by reaction with TEMPO in combination with PhIO and Bi(OTf)3 or copper (II) chloride in the presence or not of oxygen. Other primary oxidants of TEMPO such as PhI(OAc)2, mCPBA, and Oxone were unsatisfactory giving the enone in modest to low yields.

Copper-catalyzed aerobic oxidative rearrangement of tertiary allylic alcohols mediated by TEMPO

A mild method for the oxidative rearrangement of tertiary allylic alcohols to β-substituted enones using a TEMPO/CuCl2 system, in the presence of molecular sieves, is described. Depending on the substrate, CuCl2 was used in either a catalytic amount under an oxygen atmosphere or stoichiometrically. Georg Thieme Verlag Stuttgart.

A novel boron trifluoride etherate mediated deep-seated rearrangement of an α,β-epoxyketone

Acid catalysed reaction of carvone epoxide 2 resulted in dimeric products 3 and 4, in contrast to the expected ring contraction product. Reaction of β-methylcarvone epoxides 8 and 11 with acids furnished 2-acetyl-4- isopropenylcyclopentanones 9 and 14 containing a stereodefined quaternary carbon atom. On the other hand, the reaction of epoxides 8 and 11 with boron trifluoride etherate lacks the stereoselectivity and in addition, anti-epoxide 8 furnished lactone 18 via an unusual deep seated rearrangement.

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

Synthesis of chiral bicyclo[4.3.1]decanes via an intramolecular carbonyl ene-reaction

Synthesis of chiral bicyclo[4.3.1]decanes via an intramolecular acid catalysed type II ene reaction of chiral (5-isopropenylcyclohex-2- enyl)acetaldehydes derived from (R)-carvone is described.