23837-54-9Relevant academic research and scientific papers
Biomimetic synthesis of 2-substituted N-heterocycle alkaloids by one-pot hydrolysis, transamination and decarboxylative Mannich reaction
Galman, James L.,Slabu, Iustina,Parmeggiani, Fabio,Turner, Nicholas J.
, p. 11316 - 11319 (2018)
Heterocycles based on piperidine and pyrrolidine are key moieties in natural products and pharmaceutically active molecules. A novel multi-enzymatic approach based on the combination of a lipase with an α,ω-diamine transaminase is reported, opening up the synthesis, isolation and characterisation of a broad range of 2-substituted N-heterocycle alkaloids.
Synthesis of the Alkaloids, 3',4'-Dimethoxy-2-82-piperidyl)acetophenone, Julandine, and Cryptopleurine
Cragg, John E.,Herbert, Richard B.
, p. 2487 - 2490 (2007/10/02)
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).
