78480-05-4Relevant academic research and scientific papers
Synthetic studies on virantmycin. 1. Total synthesis of (±)-virantmycin and determination of its relative stereochemistry
Morimoto, Yoshiki,Matsuda, Fuyuhiko,Shirahama, Haruhisa
, p. 10609 - 10630 (2007/10/03)
The efficient and stereospecific route to the tetrahydroquinoline ring models 3 and 4 of virantmycin has been developed by means of an intramolecular nitrene addition reaction as a key step. In the NOE experiments of 4 and 3 we revealed that a ring invers
An efficient approach toward virantmycin: Stereospecific construction of tetrahydroquinoline ring system employing intramolecular nitrene-addition reaction
Morimoto, Yoshiki,Matsuda, Fuyuhiko,Shirahama, Haruhisa
, p. 6031 - 6034 (2007/10/02)
An efficient and stereospecific synthesis of the tetrahydroquinoline ring system of the structurally unique alkaloid, virantmycin (1), has been achieved using intramolecular addition reaction of nitrene to olefin as a key step.
Cyclization of Phenyl Azides with Homoallylic or Allylic Ortho Substituents and the Consequences of Triazoline Fragmentation
Smith, Peter A. S.,Chou, Shang-shing Peter
, p. 3970 - 3977 (2007/10/02)
o-(Allyloxy)phenyl azide (1) and 14 derivatives substituted on the allyl group were thermolyzed at 110-120 deg C to form benzoxazines (16), dihydroazirinobenzoxazines (17), or 3-alkenylbenzomorpholines (18, 19) through fragmentation of intermediate triazolines.With substituted allyl groups, the geometrical isomers gave the same products in the same ratio, except in the case of o-(β,γ-dimethylallyl)phenyl azide.Rearrangement by phenyl migrations occured with the β-phenylallyl compound. o-Allylphenyl azide (27a), (o-azidophenyl)acetaldehyde (27b), and o-phenyl azide (27c) required temperatures of 155-200 deg C for thermolysis and yielded 2-methylindole, oxindole, and 2-ethylbenzoxazole, respectively, by nitrene insertion.
