《Enantioselective Total Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol by Palladium-Catalyzed Domino Cyclization of Allenes Bearing Amino and Bromoindolyl Groups》 was written by Inuki, Shinsuke; Iwata, Akira; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki. Quality Control of 2-(4-Bromo-3-indolyl)acetonitrile And the article was included in Journal of Organic Chemistry on April 1 ,2011. The article conveys some information:
Enantioselective total synthesis of the biol. important indole alkaloids (+)-lysergol (I), (+)-isolyzergol (II), and (+)-lysergic acid (III) is described. Key features of these total synthesis include (1) a facile synthesis of a chiral 1,3-amino alc. via the Pd(0)- and In(I)-mediated reductive coupling reaction between L-serine-derived 2-ethynylaziridine and formaldehyde; (2) the Cr(II)/Ni(0)-mediated Nozaki-Hiyama-Kishi (NHK) reaction of an indole-3-acetaldehyde with iodoalkyne; and (3) Pd(0)-catalyzed domino cyclization of an allene bearing amino and bromoindolyl groups. This domino cyclization enabled direct construction of the C/D ring system of the ergot alkaloids skeleton, as well as the creation of the C5 stereogenic center with transfer of the allenic axial chirality to the central chirality.2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2Quality Control of 2-(4-Bromo-3-indolyl)acetonitrile) was used in this study.
2-(4-Bromo-3-indolyl)acetonitrile(cas: 89245-35-2) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Quality Control of 2-(4-Bromo-3-indolyl)acetonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts