73252-02-5Relevant academic research and scientific papers
Enantioselective syntheses and X-ray structures of (S)- and (R)-N-norlaudanidine: trace opium constituents
Zein, Ahmed L.,Dakhil, Otman O.,Dawe, Louise N.,Georghiou, Paris E.
scheme or table, p. 177 - 180 (2010/03/04)
The enantioselective synthesis of each of the enantiomers of N-norlaudanidine, a minor Papaver somniferum opium benzyltetrahydoisoquinoline alkaloid is described. This was achieved using a chiral auxiliary-mediated Bischler-Napieralski cyclization-sodium borohydride reduction strategy. The X-ray crystal structures of each of these secondary amines are reported.
Enantioselective total synthesis and X-ray structures of the tetrahydroprotoberberine alkaloids (-)-(S)-tetrahydropalmatrubine and (-)-(S)-corytenchine
Zein, Ahmed L.,Dawe, Louise N.,Georghiou, Paris E.
scheme or table, p. 1427 - 1430 (2010/10/21)
Enantioselective total syntheses and X-ray structures of both (S)-tetrahydropalmatrubine (2) and (S)-corytenchine (3) are reported for the first time. They were both derived from (S)-N-norlaudanidine, a benzyltetrahydroisoquinoline that was synthesized with high (>95% ee) enantioselectivity using a chiral auxiliary-assisted Bischler-Napieralski cyclization/reduction approach.
Anodic Amide Oxidations in the Presence of Electron-Rich Phenyl Rings: Evidence for an Intramolecular Electron-Transfer Mechanism
Moeller, Kevin D.,Wang, Po W.,Tarazi, Sharif,Marzabadi, Mohammad R.,Wong, Poh Lee
, p. 1058 - 1067 (2007/10/02)
The anodic oxidations of amides in the presence of mono-, di-, and trialkoxyphenyl rings were examined.Although literature reduction potentials suggest that these oxidations would lead to either selective aromatic ring oxidation or mixtures, the chemoselectivity of the reactions was found to be dependent on the substitution pattern of the phenyl ring.For example, the anodic oxidations of ((3-methoxyphenyl)acetyl)pyrrolidine, ((2-methoxyphenyl)acetyl)pyrrolidine, ((3-methoxy-4-(pivaloyloxy)phenyl)acetyl)pyrrolidine, and ((3,5-dimethoxy-4-(pivaloyloxy)phenyl)acetyl)pyrrolidine all led to selective methoxylation of the pyrrolidine ring.The anodic oxidations of ((4-methoxyphenyl)acetyl)pyrrolidine and ((3,4-dimethoxyphenyl)acetyl)pyrrolidine led to selective methoxylation of the benzylic carbon.Mechanistic studies indicate that both amide and aryl oxidation processes compete under the reaction conditions, but that intramolecular electron transfer leads to the selective formation of products.Evidence for this mechanism was obtained by examining the cyclic voltammogram of ((3-methoxyphenyl)acetyl)pyrrolidine, competition studies, and the preparative electrolysis of ((4-methoxyphenyl)dimethylacetyl)pyrrolidine.The methoxylated amides were cyclized to form tricyclic amides using titanium tetrachloride.
