104331-05-7Relevant academic research and scientific papers
Mild reductive cleavage of tryptophan and histidine side-chain protecting groups
Maia, Hernani L. S.,Monteiro, Luis S.,Sebastiao, Joana
, p. 1967 - 1970 (2007/10/03)
The activation potentials of the p-toluenesulfonyl and benzoyl groups as determined by cyclic voltammetry when they are linked to indole or imidazole are less negative than when these groups are linked to aliphatic amines. This makes them most suitable for side-chain protection of tryptophan and histidine, as it allows mild selective cleavage not only by controlled-potential electrolysis but also by chemical reduction using either magnesium in anhydrous methanol or mercury-activated aluminum.
DIASTEREOSPECIFICITE DE LA REACTION D'UN YLURE D'AZOMETHINE DERIVE DE LA 1-PHENYL-3-METHOXYCARBONYL-3,4-DIHYDRO-β-CARBOLINE SUR QUELQUES DIPOLAROPHILES ETHYLENIQUES
Lakhlifi, Takar,An, Nguyen Dinh,Schmitt, Gerard,Laude, Bernard,Mercier, Marie-France
, p. 169 - 176 (2007/10/02)
The synthesis of the 1-phenyl-3-methoxycarbonyl-3,4-dihydro-β-carboline was described.This compound is an azomethine ylid precursor which reacts diastereo-specifically with activated dipolarophilic olefines to yield cycloadducts involving at the same time, the β-carboline and the dehydro-nor-tropane moieties.The diastereochemistry of the 1,3-dipolar cycloaddition of cyclic azomethine ylids towards the endo rule was reinvestigated.
A GENERAL METHOD FOR THE SYNTHESIS OF INDOLES BEARING A VARIETY OF SUBSTITUENTS AT THE β-POSITION, AND ITS APPLICATION TO THE SYNTHESIS OF L-TRYPTOPHAN
Shono, Tatsuya,Matsumura, Yoshihiro,Kanazawa, Takenobu
, p. 1259 - 1262 (2007/10/02)
A general synthetic method of β-substituted indoles such as indolacetic acid, tryptamine and L-tryptophan has been exploited utilizing α-methoxylated amides, lactams, a carbamate, and sulfonamides, easily obtainable by an electrochemical method, as key intemediates.
