69496-96-4

Upstream product

• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 23837-54-9 1-(3,4-dimethoxyphenyl)-2-(piperidin-2-yl)ethan-1-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 4687-37-0 ethyl 3,4-dimethoxybenzoylacetate 
• 42245-42-1 methyl 3-(4-methoxyphenyl)glycidate 

Downstream Products

• 23365-39-1 2-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-1,6,7,8,9,9a-hexahydro-4H-quinolizin-4-one 

Relevant academic research and scientific papers

Synthesis of the Alkaloids, 3',4'-Dimethoxy-2-82-piperidyl)acetophenone, Julandine, and Cryptopleurine

Condensation of (3,4-dimethoxybenzoyl)acetic acid (2) with enzyme-generated 3,4,5,6-tetrahydropyridine (3) gives 3',4'-dimethoxy-2-(2-piperidyl)acetophenone (4) which, by reaction with p-methoxyphenylacetaldehyde followed by titanium(IV) chloride- or silicon(IV) chloride-catalysed cyclisation of the resulting enamine (6), leads to julandine (7); thallium(III) trifluoroacetate oxidation of (7) gives cryptopleurine (8) and, as a very minor product, the isomer (9).