72594-56-0Relevant academic research and scientific papers
Synthesis of a phenolic analog of aphidicolin. Diminished stereoselection in intramolecular 6-exo Heck reactions of substrates having a hydrocarbon tether
Abelman, Matthew M.,Kado, Noriyuki,Overman, Larry E.,Sarkar, Achintya K.
, p. 1469 - 1471 (1997)
Spirotetracycle 14, generated by intramolecular Heck cyclization of 13, was converted to the phenolic analog 20 of aphidicolin. That the nature of the tether connecting insertion partners can dramatically alter diastereoselection in intramolecular Heck reactions is also demonstrated.
Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation
Henry, Martyn C.,Senn, Hans Martin,Sutherland, Andrew
, p. 346 - 364 (2019/01/08)
A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.
Catalytic Cyclization of o-Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3-Benzazepines
álvarez-Pérez, Andrea,González-Rodríguez, Carlos,García-Yebra, Cristina,Varela, Jesús A.,O?ate, Enrique,Esteruelas, Miguel A.,Saá, Carlos
supporting information, p. 13357 - 13361 (2015/11/09)
A novel osmium-catalyzed cyclization of o-alkynyl phenethylamines to give 3-benzazepines is reported. The procedure allows the straightforward preparation of a broad range of dopaminergic 3-benzazepine derivatives. Mechanistic investigations revealed that the process takes place via osmacyclopropene intermediates, which were isolated and characterized by X-ray crystallography.
A short, efficient, synthetic pathway to the 6,7,8,9-tetrahydro-5h-dibenz[d,f]azonine system
Brandt, Steven,Marfat, Anthony,Helquist, Paul
, p. 2193 - 2194 (2007/10/11)
The intramolecular, nickel-promoted coupling of a bis[β-(o-iodophenyl)ethyl] amine produces a dibenzazonine of the type exemplified by several naturally occurring compounds and which serve as biosynthetic precursors of the Erythrina alkaloids.
