85696-84-0

Upstream product

• 67-56-1 methanol 
• 50314-05-1 3-chloro-2-(2'-propenyl)cyclohex-2-enone 
• 42738-68-1 2-allylcyclohexane-1,3-dione 
• 149-73-5 trimethyl orthoformate 
• 504-02-9 1,3-cylohexanedione 
• 106-95-6 allyl bromide 
• 77-78-1 dimethyl sulfate 
• 32774-70-2 2-allyl-3-hydroxycyclohex-2-en-1-one 
• 186581-53-3 diazomethane 

Downstream Products

• 143537-45-5 (6-Allyl-5-methoxy-cyclohexa-1,5-dienyloxy)-trimethyl-silane 
• 1032268-47-5 C₁₆H₁₈BrNO₂ 
• 38019-50-0 2-allyl-cyclohex-2-enone 
• 202862-62-2 (S)-3-ethenyl-2-(2-propenyl)-2-cyclohexen-1-ol 
• 1401226-17-2 C₁₈H₂₂O₃ 
• 1401226-05-8 3-(1-ethoxyethenyl)-2-allyl-2-cyclohexen-1-ol 
• 1401226-07-0 (S)-2-[(2-allyl-3-vinylcyclohex-2-en-1-yl)oxy]phenol 
• 1401226-11-6 (S)-2-[(2-allyl-3-vinylcyclohex-2-en-1-yl)oxy]benzonitrile 
• 1401226-12-7 (S)-2-[(2-allyl-3-vinylcyclohex-2-en-1-yl)oxy]benzaldehyde 
• 1401226-16-1 (S)-2-[(2-allyl-3-vinylcyclohex-2-en-1-yl)oxy]phenyl formate 
• 202862-61-1 3-ethenyl-2-(2-propenyl)-2-cyclohexen-1-one 
• 1401226-47-8 3-(1-ethoxyethenyl)-2-allyl-2-cyclohexen-1-one 
• 92035-62-6 2-Allyl-1-(but-3-enyl)-cyclohex-1-en-3-on 
• 150456-45-4 3-Methoxy-6-methyl-2-(2-propenyl)-2-cyclohexenone 

Relevant academic research and scientific papers

Developing the Saegusa-Ito Cyclisation for the Synthesis of Difluorinated Cyclohexenones

Palladium(II)-catalysed cycloalkenylation (Saegusa-Ito cyclisation) has been used for the first time to transform difluorinated silylenol ethers to difluorinated cycloalkenones under mild conditions. The silylenol ether precursors were prepared in two high-yielding steps from trifluoroethanol, and cyclised in moderate to good yields. A combination of air and copper(I) chloride in acetonitrile gave the turnover of the initial palladium(II) salt, whereas the provision of an oxygen atmosphere ensured more rapid reaction. Annulations required a minimum level of substitution on the chain, but failed when the alkene was substituted. Annelations allowed a range of n,6-bicyclic systems to be prepared and afforded three products, in which heterocycles were fused to the new cyclohexenone. The least substituted system explored underwent cyclisation followed by terminal oxidation to a cyclic enal, which corresponded to a Wacker product of unusual regiochemistry.

From chiral ortho-benzoquinone monoketals to nonracemic indolinocodeines through diels-alder and cope reactions

The S-dienol (-)-4 containing 10 carbons and one oxygen of the final product was prepared in 98.6% ee and 39% yield from cyclohexan-1,3-dione. It was attached to the aromatic ring as a monoether of catechol S-(-)-6 and subsequently subjected to oxidative ketalization in methanol. The allylated phenanthrofuran obtained was selectively oxidized at the terminal double bond. The fifth ring was completed by a one-pot amidation-cyclization process promoted by palladium acetate. The final homochiral indolinocodeine (-)-31 was obtained in 16 steps and 3.6% overall yield from cyclohexan-1,3-dione.

Toward the total synthesis of palhinine A: Expedient assembly of multifunctionalized isotwistane ring system with contiguous quaternary stereocenters

The stereoselective, expedient assembly of the key functionalized isotwistane (bridged tricyclo[4.3.1.03,7]decane) system, 5/6/6 ring, with contiguous quaternary stereocenters in Lycopodium alkaloid palhinine A and its analogues via an intramol

An efficient method for construction of the angularly fused 6,3,5-tricyclic skeleton of mycorrhizin A and its analogues

(Chemical Equation Presented) The angularly fused 6,3,5-tricyclic system is readily generated via a cascade cyclization under acid promotion. The reaction proceeds at room temperature with high stereochemical fidelity from the electrophilic center of the

Reaction of Phosphonate-Stabilized Carbanions with Cyclic Enones Bearing a β-Leaving Group

Reaction between α-lithiated alkylphosphonic esters and α,β-unsaturated cyclopentenones and cyclohexenones carrying a heteroatom substituent Y in the β-position was studied.Complete chemoselectivity was observed as a function of substituent Y.For Y = OMe exclusive addition-elimination at the β-carbon was observed, yielding α,β-unsaturated δ-ketophosphonates.The β-chloro-substituted substrates (Y = Cl) derived from cyclohexenone reacted exclusively at the carbonyl carbon, yielding (2-hydroxyalkyl)phosphonates with the retained chlorovinyl function.The alcohols, depending on the conditions, could be dehydrated to two different products.The reaction of 3-chlorocyclopent-2-en-1-one with diethyl (lithiomethyl)phosphonate occured at the β-carbon, but the ketophosphonate product was isolated in a stable enolic form.

The synthesis of mycophenolic acid

A new synthesis of mycophenolic acid 1, has been accomplished using silyloxy-1,3-cyclohexadiene 9 which undergoes cycloaddition to dimethyl acetylenedicarboxylate and subsequent elimination of ethylene (Alder-Rickert reaction) to give the trisubstituted dimethyl phthalate 11. After conversion of 11 to phthalide 16, the (E)-4-methyl-4-hexenoic acid side-chain was constructed via an orthoester Claisen rearrangement using allylic alcohol 19 and triethyl orthoacetate.

First unambiguous total synthesis of hericenone A: Proposed structure revised

Hericenone A has been synthesized by an unambiguous route involving a Diels-Alder reaction and the well known regioselective NaBH4-reduction of the phthalates.