85710-66-3

Upstream product

• 1072085-41-6 (R)-5-Isopropyl-1,2-dimethyl-cyclohex-2-enol 
• 127911-96-0 (1R,5R)-5-Isopropenyl-1,2-dimethyl-cyclohex-2-enol 
• 852930-25-7 (R)-2-methylcarveol 
• 917-64-6 methyl magnesium iodide 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 143612-00-4 (-)-(1S,4S,6S)-4-isopropenyl-1,6-dimethyl-7-oxabicyclo[4.1.0]heptan-2-one 
• 6485-40-1 (R)-Carvone 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 127400-23-1 5-(1-(bromomethyl)-1-methoxyethyl)-2,3-dimethylcyclohex-2-en-1-one 
• 127400-28-6 5-(1-(bromomethyl)-1-acetoxyethyl)-2,3-dimethylcyclohex-2-en-1-one 
• 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 
• 14087-70-8 (+)-Dihydrochrysanthemolactone 
• 85710-70-9 (5S)-5-(1-Chloro-1-methylethyl)-2-hydroxy-3-methoxy-2,3-dimethylcyclohexan-1-one 
• 85710-69-6 (5S)-5-(1-Chloro-1-methylethyl)-3-hydroxy-2-methoxy-2,3-dimethylcyclohexan-1-one 
• 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 
• 868387-84-2 (-)-(2S,4S)-2-acetyl-4-isopropenyl-2-methylcyclopentanone 
• 328934-89-0 (-)-(3R,5R)-3-(2-hydroxyethyl)-5-isopropenyl-2,3-dimethylcyclohexane 

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

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.

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.

Lewis acid promoted oxidative rearrangement of tertiary allylic alcohols with the PhIO/TEMPO system

A mild and environmentally friendly method for Lewis acid catalyzed oxidative rearrangement of tertiary allylic alcohols to β-disubstituted enones by the TEMPO/PhIO system is described. Bismuth triflate was found to be the most efficient catalyst for the majority of the substrates tested except for tertiary vinyl carbinols which could be transformed to enals in fair yields only when Re2O7 was used as catalyst. A plausible mechanism for this oxidative rearrangement is discussed. Georg Thieme Verlag Stuttgart.

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

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.

A convenient deoxygenation fo α,β-epoxy ketones to enones

A new and efficient methodology for the deoxigenation of α,β-epoxy ketones to enones has been developed, using aminoiminomethanesulfinic acid (thioulea dioxide) as the reducing agent under phase transfer conditions. The epoxides of mesityl oxide, isophorane (-)-carvone, (+)-6-methyl-carvone, (+)-6-ethyl-carvone and (-)-myrtenal, were converted into their respectives enones in good to excellent yields.