82044-96-0

Upstream product

• 6485-40-1 (R)-Carvone 
• 870245-36-6 (R)-5-[3-(3-methoxyphenoxy)prop-1-en-2-yl]-2-methylcyclohex-2-en-1-one 
• 870245-35-5 (R)-5-[3-(3-hydroxyphenoxy)prop-1-en-2-yl]-2-methylcyclohex-2-en-1-one 
• 870245-37-7 (R)-5-[3-(3-isopropoxyphenoxy)prop-1-en-2-yl]-2-methylcyclohex-2-en-1-one 
• 870245-38-8 (R)-5-[3-(3-benzoyloxyphenoxy)prop-1-en-2-yl]-2-methylcyclohex-2-en-1-one 

Downstream Products

• 136066-42-7 (5R)-5-(1-Hexen-2-yl)-2-methyl-2-cyclohexen-1-one 
• 870245-35-5 (R)-5-[3-(3-hydroxyphenoxy)prop-1-en-2-yl]-2-methylcyclohex-2-en-1-one 
• 870245-38-8 (R)-5-[3-(3-benzoyloxyphenoxy)prop-1-en-2-yl]-2-methylcyclohex-2-en-1-one 
• 912279-64-2 (R)-5-[1-(4-Ethyl-piperazin-1-ylmethyl)-vinyl]-2-methyl-cyclohex-2-enone 
• 912279-67-5 (R)-5-[1-(4-Benzyl-piperazin-1-ylmethyl)-vinyl]-2-methyl-cyclohex-2-enone 
• 82045-01-0 5-(4-keto-6-methyl-1-hepten-2-yl)-2-methyl-2-cyclohexenone 
• 82045-00-9 (R)-2-Methyl-5-[2-(4-methyl-2-oxo-pentyl)-oxiranyl]-cyclohex-2-enone 
• 82044-99-3 (R)-5-[2-(2-Hydroxy-4-methyl-pentyl)-oxiranyl]-2-methyl-cyclohex-2-enone 
• 17015-33-7 (+)-bilobanone 
• 1360591-96-3 2-methyl-5-(1-morpholin-4-ylmethylvinyl)cyclohex-2-enone 
• 1127117-21-8 5-(3-(diethylamino)prop-1-en-2-yl)-2-methylcyclohex-2-enone 

Relevant academic research and scientific papers

Newly synthesized (R)-carvone-derived 1,2,3-triazoles: structural, mechanistic, cytotoxic and molecular docking studies

In the current study, natural (R)-carvone was used as starting material for the efficient synthesis of several 1,2,3-triazole derivatives. The produced products were obtained in good yields and characterized by 1H and 13C NMR and HRM

Synthesis of carvone-derived 1,2,3-triazoles study of their antioxidant properties and interaction with bovine serum albumin

Natural L-carvone was utilized as a starting material for an efficient synthesis of some terpenyl-derived 1,2,3-triazoles. Chlorination of carvone, followed by nucleophilic substitution with sodium azide resulted in the preparation of 10-azidocarvone. Sub

Type-II Pauson-Khand reaction of 1,8-enyne in the attempt of building 7/5 ring of (-)-caribenol A and DFT understanding

An attempt to access the fused 7/5 ring of the highly biologically active terpenoid caribenol A by employing intramolecular Pauson-Khand reaction of 1,8-enyne gave bridged 8-5 ring, the type-II Pauson-Khand reaction product. DFT study has been carried out

Continuous Flow Organocatalytic Chlorination of Alkenes

A regioselective anti-dichlorination and allylic chlorination of isolated double bonds is described. Such chlorination reactions benefit from a combination of methyl phenyl sulfoxide and TMSCl. The method has been appropriately adjusted to fit the continuous flow technology requirements, aiming to a broader industrial implementation for the synthesis of pharmaceutically important compounds. Towards the same direction, a catalytic protocol has been developed, using sub-stoichiometric amount of sulfoxide and environmentally friendly H2O2 as the stoichiometric oxidant, with comparable efficacy.

SYNTHESIS OF THAPSIGARGIN, NORTRILOBOLIDE, AND ANALOGS THEREOF

The present invention relates to the preparation of compounds of Formula I, including thapsigargin, nortrilobolide and 8-O-debutanoyl-thapsigargin from commercially available (R)-(-)-carvone via synthetic intermediate compound of formula 12 by pinacol coupling and in situ lactonization.

A Concise, Efficient and Scalable Total Synthesis of Thapsigargin and Nortrilobolide from (R)-(?)-Carvone

A concise, efficient and scalable synthesis of thapsigargin and nortrilobolide from commercially available (R)-(?)-carvone was developed. Our synthetic strategy is inspired by nature’s carbon-carbon bond formation sequence, which facilitates the construction of a highly functionalized sesquiterpene lactone skeleton in five steps via an enantioselective ketone alkylation and a diastereoselective pinacol cyclization. We envision that this strategy will permit the construction of other members of the family, structural analogs and provide a practical synthetic route to these important bioactive agents. In addition, we anticipate that the prodrug Mipsagargin, which is currently in late-stage clinical trials for the treatment of cancer, will also be accessible via this strategy. Hence, the limited availability from natural sources, coupled with an estimated demand of one metric ton per annum for the prodrug, provides a compelling mandate to develop practical total syntheses of these agents.

Gram Scale Syntheses of (-)-Incarvillateine and Its Analogs. Discovery of Potent Analgesics for Neuropathic Pain

(-)-Incarvillateine (INCA) is the major antinociceptive component of Incarvillea sinensis, which has been used to treat rheumatism and relieve pain in traditional Chinese medicine. We have developed a concise and general synthetic approach for INCA, which

A mild and efficient method for the synthesis of a new optically active diallyl selenide and its catalytic activity in the allylic chlorination of natural terpenes

A mild and convenient method for the synthesis of a new optically active bis(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)selenide 1 from the corresponding bicyclic terpene is described. The structure of the obtained organoselenium compound was establis

Obtained Incarvillea esterine analogs and method for preparation thereof and use in the analgesic medicament

The invention relates to an analogue of natural product incarvillateine with a novel structure of containing a cyclobutane dimer frame, including a compound with a general formula I, a compound with a general formula II and pharmaceutical salts thereof, as well as preparation methods of the compounds and application thereof in analgesics. In the general formula I, R1 is hydrogen or various alkyl substituent groups or various acyl substituent groups or various aryl groups, such as methyl, ethyl, propyl, butyl, allyl, benzyl, cyclopropyl methyl, acetyl, benzoyl and phenyl; R2 and R3 are respectively hydrogen or methyl, or R2 and R3 are methylene in common. In the general formula II, R4 is hydrogen or various alkyl substituent groups or various acyl substituent groups or various aryl groups, such as methyl, ethyl, propyl, butyl, allyl, benzyl, cyclopropyl methyl, acetyl, benzoyl and phenyl; and n is 0-4. The compounds have excellent pain relieving effect.

Total synthesis of alotaketal A

The total synthesis of the cAMP signaling pathway activator (-)-alotaketal A is reported. A convergent approach to the unusual alotane sesterterpenoid skeleton was employed, exploiting a remarkable LiDBB-mediated coupling of an (R)-carvone-derived δ-lactone with an allyl bromide side chain, followed by spiroacetalization.