158616-08-1Relevant academic research and scientific papers
One-Pot Synthesis and Conformational Analysis of Six-Membered Cyclic Iodonium Salts
Caspers, Lucien D.,Spils, Julian,Damrath, Mattis,Lork, Enno,Nachtsheim, Boris J.
, p. 9161 - 9178 (2020/08/14)
Two one-pot procedures for the construction of carbon-bridged diaryliodonium triflates and tetrafluoroborates are described. Strong Br?nsted acids enable the effective Friedel-Crafts alkylation with diversely substituted o-iodobenzyl alcohol derivatives, providing diphenylmethane scaffolds, which are subsequently oxidized and cyclized to the corresponding dibenzo[b,e]iodininium salts. Based on NMR investigations and density functional theory (DFT) calculations, we could verify the so-far-undescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge.
Intramolecular heck insertion of a diene-allylic amination cascade to synthesize a 2-alkenyl-3,4-fused indole structure
Kuribara, Takahito,Ueda, Jun,Tanaka, Yuito,Nakajima, Masaya,Harada, Shingo,Nemoto, Tetsuhiro
, p. 1175 - 1190 (2019/07/31)
– Iodoanilines bearing a diene side-chain at the 3-position were converted to tricyclic fused indole derivatives under palladium catalysis. This cascade reaction proceeds through an intramolecular Heck insertion of the diene, followed by an allylic amination reaction sequence. Experimental and computational studies indicated that K3S-allylpalladium complex-mediated substitution was operative for the latter cyclization.
Enantioselective formal synthesis of (?)-aurantioclavine using Pd-catalyzed cascade cyclization and organocatalytic asymmetric aziridination
Nakano, Shun-ichi,Hamada, Yasumasa,Nemoto, Tetsuhiro
supporting information, p. 760 - 762 (2018/01/22)
The enantioselective formal synthesis of (?)-aurantioclavine is described. The core tricyclic skeleton was synthesized using a Pd-catalyzed Heck insertion–allylic amination cascade. The stereocenter was constructed by a highly enantioselective organocatal
Intriguing substituent effect in modified Hoveyda-Grubbs metathesis catalysts incorporating a chelating iodo-benzylidene ligand
Barbasiewicz, Michal,Blocki, Krzysztof,Malinska, Maura,Pawlowski, Robert
supporting information, p. 355 - 358 (2013/02/22)
A series of modified Hoveyda-Grubbs catalysts incorporating a chelating iodo-benzylidene ligand were prepared and characterized. The presence of electron-withdrawing ring substituents in the para position to the iodide was found to decrease the catalytic activity, revealing that dissociation of the Ru...I-Ar bond is not the rate-determining step.
Synthesis and Cytotoxicity of Amino-seco-DSA: An Amino Analogue of the DNA Alkylating Agent Duocarmycin SA
Tercel, Moana,Gieseg, Michael A.,Denny, William A.,Wilson, William R.
, p. 5946 - 5953 (2007/10/03)
This paper describes the synthesis of methyl 5-amino-1-(chloromethyl)-3-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-1,2-dihydro- 3H-pyrrolo[3,2-e]indole-7-carboxylate 8, an amino analogue of the anticancer antibiotic and potent DNA minor groove alkylating agen
Tandem radical cyclisations: Synthesis of lysergic acid derivatives
Ozlu,Cladingboel,Parsons
, p. 2183 - 2206 (2007/10/02)
A novel free radical cyclisation approach for the synthesis of lysergic acid analogues has been investigated. The homolytic cleavage of carbon- bromine bond, mediated by tri-n-butyltin hydride, led to the development of a method for the construction of 3,
