1919-00-2

Upstream product

• 118668-59-0 2-Bromo-1-methoxy-1-prop-2-ynyloxy-cyclohexane 
• 118668-60-3 2-Bromo-1-ethoxy-1-prop-2-ynyloxy-cyclohexane 
• 15174-78-4 2,4,5,6,7,7a-Hexahydro-3-methyl-1-benzofuran-2-on 
• 83686-90-2 1-(2-(trimethylsilyloxy)-1(Z)-cyclohexen-1-yl)-propanone 
• 89880-34-2 2-[1-Hydroxy-1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclohexanone 
• 286-20-4 cyclohexane-1,2-epoxide 
• 15210-05-6 c-3a,4,5,6,7,t-7a-hexahydro-r-3-hydroxy-3-methyl-2(3H)-benzofuranone 
• 15210-05-6 t-3a,4,5,6,7,c-7a-hexahydro-r-3-hydroxy-3-methyl-2(3H)-benzofuranone 
• 3908-31-4 1-Isopropenyl-1-cyclohexanol 
• 108-94-1 cyclohexanone 
• 72952-62-6 Ethyl 2-<1-(ethoxycarbonyl)-2-oxocyclohexyl>propionate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 1122-84-5 1-ethoxycyclohexene 
• 931-57-7 1-methoxy-cyclohex-1-ene 

Downstream Products

• 15210-14-7 (RS)-3-methyl-7a-hydroxy-4,5,6,7-tetrahydro-7aH-benzofuran-2-one 

Relevant academic research and scientific papers

A New Synthetic Route to 2,5-Dihydrofurans

ButOK-dimethyl sulfoxide-catalysed selective isomerization of 3-methylene tetrahydrofurans 1 provides a new convenient route to 2,5-dihydrofuran 2 precursors of furan-2(3H)-ones 8 or furans 4 or 9.

Synthetic models related to methoxalen and menthofuran-cytochrome P450 (CYP) 2A6 interactions. Benzofuran and coumarin derivatives as potent and selective inhibitors of CYP2A6

Human microsomal cytochrome P450 (CYP) 2A6 contributes extensively to nicotine detoxication but also activates tobacco-specific procarcinogens to mutagenic products. We prepared a series of benzofuran and coumarin derivatives that have inhibitory effects on the activity of human CYP2A6. The reported compounds methoxalen and menthofuran had potent inhibitory effects on the activity of CYP2A6 with IC50 values of 0.47 μM and 1.27 μM, respectively. Synthetic benzofuran (4-methoxybenzofuran: IC50=2.20 μM) and coumarin (5-methoxycoumarin: IC50=0.13 μM and 6-methoxycoumarin: IC50=0.64 μM) derivatives, which have more selective effects than those of methoxalen and menthofuran, exhibited comparable activities against CYP2A6. These compounds can be used as a lead compounds in the design of CYP2A6 inhibitor drugs to reduce smoking and tobacco-related cancers.

Dimerization of butenolide structures. A biomimetic approach to the dimeric sesquiterpene lactones (±)-biatractylolide and (±)- biepiasterolide

The biomimetic synthesis of the bisesquiterpene lactones (±)-biatractylolide 1 and (±)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.

Studies towards the biomimetic synthesis of bisesquiterpene lactones

A possible biomimetic connection between atractylolide, hydroxyatractylolide and biatractylolide and biepiasterolide has been demonstrated by efficiently generating the biatractylolide and biepiasterolide core structures from atractylolide and hydroxyatra

Preparation of α-Hydroxy-γ-lactones and their Application in the Synthesis of α,β-Butenolides, α-Alkylidene-γ-lactones and Furans

A straightforward synthesis of α-hydroxy-γ-butyrolactones was carried out by condensation reaction of the lithium anion of ethoxyethyl-protected cyanohydrins with epoxides, followed by acidic treatment.Synthetic applications of these synthons in the preparation of interesting α,β-butenolides, α-alkylidene-γ-lactones and furans are described.

FURANNULATION via RADICAL CYCLISATION

A three step 4-methyl furan annulation sequence is described via the radical cyclisation of bromo-acetal 3 to 2-alkoxy-4-methylene tetrahydrofuran 4

Photooxygenation of 1-Vinylcycloalkenes. The Competition between "Ene" Reaction and Cycloaddition of Singlet Oxygen

The competition between the "ene" reaction and 1,4-cycloaddition reaction of 1O2 in a series of 1-vinylcycloalkenes (n = 5-10, 12) and 1-isopropenylcycloalkenes (n = 6-8) was studied.Ring size had a profound effect.When n = 5 or 7, products of the "ene" reaction predominated, but as ring size increased cycloaddition competed closely with the "ene" process, the crossover being at ring size 10. 1-Vinylhexenes constituted an exception with 1,4-cycloaddition greatly predominant. "Ene" products were almost exclusively conjugated diene hydroperoxides or secondary products derived from them; small amounts of unconjugated diene hydroperoxides were formed only when n = 9, 10, or 12.The influence of ring size of the "ene" to cycloaddition product ratio is compared with the rates of photooxygenation and the degree of syn-regiospecificity exhibited by (Z)-1-methylcycloalkenes and attributed to the same mainly conformational factors, as is the geometry of the "ene" products.The 1,4-cycloaddition products were converted to furans by means of ferrous sulfate.

New Route for Synthesis of Furan Derivatives from Protected α-Ketols and Ketones. A Total Synthesis of Furoventalene

Reaction of acetonyl tetrahydropyranyl ether (1) with ketones (2a-d) in the presence of lithium di-isopropylamide and zinc chloride produces the cross-aldol condensation products (3a-d), which are transformed into 3-methylfurans (4a-d), by treatment with

FLASH VACUUM THERMOLYSIS OF β-KETO-TRIMETHYLSILYL-ENOL-ETHERS. SYNTHESIS OF ALLENIC AND FURANIC DERIVATIVES

Thermolysis at 800 deg C of a series of β-keto-trimethylsilyl-enol-ethers allows the elimination of a trimethylsilanol molecule through a 1,5 rearrangement.The reduction products are furanic derivatives, which are obtained in often good yields through an allenic intermediate, which has been isolated.