79893-96-2Relevant academic research and scientific papers
Biomimetic synthesis of nitraramine
Wanner,Koomen
, p. 5634 - 5637 (1995)
The synthesis of a possible biosynthetic precursor (9) of nitraramine (1) is described, utilizing N-Boc-piperidone as an equivalent of didehydropiperidine 4. Heating this reactive, achiral intermediate 9 in aqueous solution results in the stereoselective formation of natural nitraramine via three successive cyclization reactions. Since nitraramine and several other Nitraria alkaloids are obtained from Nitraria species in racemic form, this synthesis provides additional support for our hypothesis of non-enzyme-catalyzed formation of these alkaloids.
Biomimetically relevant self-condensations of C5 units derived from lysine
Salame, Rim,Gravel, Edmond,Retailleau, Pascal,Poupon, Erwan
experimental part, p. 2522 - 2528 (2010/07/05)
In various conditions, dimerization of pentanedial-derived units gives rise to interesting skeletons, which are reminiscent of alkaloids known to be biosynthesized in Nature via lysine metabolism. The Royal Society of Chemistry 2010.
Synthesis of the brominated marine alkaloids (±)-arborescidine A, B and C
Burm, Brigitte E.A.,Meijler, Michael M.,Korver, Jacco,Wanner, Martin J.,Koomen, Gerrit-Jan
, p. 6135 - 6146 (2007/10/03)
A straightforward synthesis of the brominated marine alkaloids arborescidine A (1), B (2) and C (3), starting from 6-bromo-(N-methyl) trypatamine is described. An equilibrium, under both basic and acidic conditions was found to exist between the trans- and cis-isomers 3 and 4. Spectral data indicated that the structure of isomer 4 does not correspond with the compound identified as arborescidine D recently isolated from the marine tunicate Pseudodistoma arborescens.
