1108084-76-9

Upstream product

• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 504-02-9 1,3-cylohexanedione 
• 2859-78-1 4-Bromoveratrole 
• 58775-54-5 (+/-)-3-ethoxy-6-(prop-2-enyl)-cyclohex-2-en-1-one 
• 591-87-7 Allyl acetate 
• 1108084-55-4 3-ethoxy-6-(3',4'-dimethoxyl-phenyl)cyclohex-2-en-1-one 
• 106-95-6 allyl bromide 

Downstream Products

• 1108084-89-4 2-(1-(3,4-dimethoxyphenyl)-4-ethoxy-2-oxocyclohex-3-enyl)acetaldehyde 
• 440361-90-0 4-allyl-4-(3,4-dimethoxyphenyl)cyclohex-2-enone 

Relevant academic research and scientific papers

Palladium-catalyzed asymmetric direct intermolecular allylation of α-aryl cyclic vinylogous esters: Divergent synthesis of (+)-oxomaritidine and (?)-mesembrine

We demonstrate that α-aryl cyclic vinylogous esters are competent substrates in the direct intermolecular Pd-catalyzed asymmetric allylic alkylation, enabling a straightforward enantioselective synthesis of 6-allyl-6-aryl-3-ethoxycyclohex-2-en-1-ones, common motifs embedded in numerous structurally diverse natural products. As an initial demonstration of the utility of this protocol, the first catalytic enantioselective total synthesis of (+)-oxomaritidine and an improved five-step catalytic enantioselective synthesis of (?)-mesembrine have been completed divergently.

Palladium-Catalyzed α-Arylation of Cyclic Vinylogous Esters for the Synthesis of γ-Arylcyclohexenones and Total Synthesis of Aromatic Podocarpane Diterpenoids

Described is a method for the formal γ-arylation of cyclohexenones allowing synthesis of a remote all-carbon quaternary center. The process involves the palladium-catalyzed α-arylation of a α-substituted cyclic vinylogous ester followed by the Stork-Danheiser transposition. The synthetic utility of this protocol is featured in the total syntheses of (±)-12-hydroxy-13-methylpodocarpa-8,11,13-trien-3-one, (±)-3β,12-dihydroxy-13-methylpodocarpane-8,11,13-triene, and (±)-O-methyl nimbinone.

Palladium-catalyzed sequential arylation and allylic alkylation of highly functionalized ketones: A concise synthesis of mesembrine

(Chemical Equation Presented) An unprecedented palladium-catalyzed sequential procedure toward arylation and allylic alkylation of highly functionalized cyclohexenones was developed. This new protocol leads to useful building blocks containing a benzylic