91781-46-3

Upstream product

• 6485-40-1 (R)-Carvone 
• 74-88-4 methyl iodide 
• 138812-34-7 (R)-6-methylcarvone 

Downstream Products

• 331961-14-9 (2S,3R,6R)-2,6-dimethyl-3-(prop-1-en-2-yl)cyclohexan-1-one 
• 331961-46-7 (2S,3R,6S)-2,6-dimethyl-3-(prop-1-en-2-yl)cyclohexan-1-one 
• 691871-02-0 (5R,6S)-5-Isopropenyl-2,6-dimethyl-1-pent-4-enyl-cyclohex-2-enol 
• 1030607-37-4 (5R,6S)-2,6-dimethyl-5-((R)-2-methyloxiran-2-yl)cyclohex-2-enone 
• 213315-08-3 Acetic acid (1R,2R,5R,6S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohexyl ester 
• 213315-07-2 (1R,2R,5R,6S)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-isopropenyl-2,6-dimethyl-cyclohexanol 
• 213315-03-8 (4R,5S,6R)-6-(2-Bromo-1-ethoxy-ethoxy)-4-isopropenyl-1,5-dimethyl-cyclohexene 
• 213315-06-1 (1R,2R,5R,6S)-2-(2-Hydroxy-ethyl)-5-isopropenyl-2,6-dimethyl-cyclohexanol 
• 331961-25-2 2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethyl toluene-4-sulfonate 
• 331961-17-2 ((2S,3R,6R)-1-Acetoxy-3-isopropenyl-2,6-dimethyl-cyclohexyl)-acetic acid ethyl ester 
• 331961-38-7 (1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarboxylic acid methyl ester 
• 331961-29-6 (1R,2R,3S,4R)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of (-)-Picrotoxinin by Late-Stage Strong Bond Activation

We report a concise, stereocontrolled synthesis of the neurotoxic sesquiterpenoid (-)-picrotoxinin (1, PXN). The brevity of the route is due to regio-and stereoselective formation of the [4.3.0] bicyclic core by incorporation of a symmetrizing geminal dim

Total Synthesis of (?)-Indoxamycins A and B

The concise total syntheses of (?)-indoxamycins A and B is reported. The chemistry features a seven-step preparation of a highly congested [5.5.6] tricyclic advanced common intermediate from a readily available R-carvone derivative. Key steps involve a Pa

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.

Silver(I)-catalyzed ring-contractive rearrangement: A new entry to 5-alkylidene-2-cyclopentenones

A novel silver(I)-catalyzed ring-contractive rearrangement of 5-substituted 6-diazo-2-cyclohexenones has been developed, providing a new and efficient access to 5-alkylidene-2-cyclopentenones. The AgOTf-catalyzed reaction proceeds through metal-carbenoid formation followed by endocyclic allyl [1,2] migration with excellent stereoselectivity and broad substrate scope.

Efficient synthesis of (1R,4S,6R)-4-Isopropenyl-1,3,3-trimethyl-7- oxabicyclo[4.1.0]heptan-2-one

A simple and convenient one-pot synthesis of (1R,4S,6R)-4-isopropenyl-1,3, 3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one was developed consisting in a thermodynamic methylation of carvone (NaH, MeI, THF, 20°C) followed by the epoxidation with alkalinized hy

Enantioselective synthesis of a key A-ring intermediate for the preparation of 1α,25-dihydroxyvitamin D3

A novel approach to the key A-ring α, β-unsaturated aldehyde 1, an important intermediate for the preparation of 1α,25-dihydroxyvitamin D3, has been developed. The strategy started from the inexpensive starting material (R)-carvone with an ene reaction serving as the key step toward the potential synthesis of vitamin D3 analogues bearing the modification at the C-2 position.

Enantiospecific construction of the BC-ring system of taxanes

Two alternative approaches to the BC-ring system of taxanes, suitable for generating both enantiomeric forms of taxanes, starting from the readily and abundantly available monoterpene (R)-carvone employing a ring-closing metathesis reaction as key step, are described.

Palladium-mediated ring closure reactions. Facile syntheses of enantiopure bicyclic and tricyclic alkenones

(R)-Carvone was used as a chiral building block. Regio- and stereoselective alkylations at C6 and C2 of (R)-carvone and (R)-5-isopropyl-2-methyl-2-cyclohexenone [derived from the hydrogenation of (R)-carvone] followed by palladium-mediated ring closures a

An enantiospecific approach to pinguisanes from (R)-carvone. Total synthesis of (+)-pinguisenol

Enantiospecific total synthesis of (+)-pinguisenol 1, a sesquiterpene containing a cis-1,2,6,7-tetramethylbicyclo[4.3.0]nonane carbon framework incorporating two vicinal quaternary carbon atoms and four cis-oriented methyl groups on four contiguous carbon atoms, isolated from a liverwort, is described. The orthoester Claisen rearrangement of the allyl alcohol 9, obtained from (R)-carvone, generates the ester 12. Intramolecular cyclopropanation of the diazo ketone 13, derived from the ester 12, furnishes the tricyclic ketone 7. Degradation of the isopropenyl group followed by regioselective reductive cyclopropane ring cleavage transforms compound 7 into the hydroxy ketone 21. Wblff-Kishner reduction of the hydroxy ketone 21 followed by oxidation and Grignard reaction furnishes pinguisenol (+)-1. The Royal Society of Chemistry 2000.

A new route to 2,7- and 7-functionalized labdanes

A new route for the synthesis of 2,7- and 7-functionalized labdanes starts from (R)-carvone (1). 11-Nordrim-7-en-9-one (15) is an appropriate starting material for the total synthesis of hispanone (21), a biologically active furolabdane isolated from the