74809-42-0Relevant academic research and scientific papers
Intramolecular radical additions to quinolines
Harrowven, David C.,Sutton, Benjamin J.,Coulton, Steven
, p. 2907 - 2910 (2007/10/03)
This paper is concerned with intramolecular radical additions to quinolines. Radical additions to C-2, C-3 and C-4 of a quinoline have all been shown to proceed under neutral conditions. In each case formation of heteroaromatic products, rather than dihydroquinolines, was observed (implicating the so called oxidative tin hydride pathway).
The first total synthesis of toddaquinoline, an alkaloid from Toddalia asiatica
Harrowven, David C.,Nunn, Michael I.T.,Blumire, Nigel J.,Fenwick, David R.
, p. 4447 - 4454 (2007/10/03)
The paper describes the first total synthesis of toddaquinoline, an alkaloid from the root bark of Formosan Toddalia asiatica. The key step is cobalt(I) mediated radial cyclisation to a pyridine. Cobalt appears to play a dual role in the reaction, firstly initialising homolysis of the carbon to halogen bond then acting as a Lewis acid to promote cyclisation to C-6. Other approaches examined are also outlined. These include a photocyclisation of an azastilbene; a cyclisation induced by halogen to metal exchange and a tin mediated radical cyclisation.
A total synthesis of toddaquinoline exposes a dual role for cobalt in radical additions to pyridines
Harrowven,Nunn,Blumire,Fenwick
, p. 6681 - 6683 (2007/10/03)
This paper describes the first total synthesis of toddaquinoline, an alkaloid from the root bark of Formosan Toddalia asiatica. Importantly, the synthesis has exposed a dichotomy in radical reactions mediated by tin and cobalt(I) that involve additions to pyridines. Our observations suggest that cobalt plays a dual role in such reactions: Firstly initiating homolysis of the carbon to halogen bond, then acting as a Lewis acid to promote radical additions to the carbon centre adjacent to nitrogen. (C) 2000 Elsevier Science Ltd.
The intramolecular addition of an aryl radical to a pyridine provides a short entry to toddaquinoline
Harrowven, David C.,Nunn, Michael I.T.
, p. 5875 - 5876 (2007/10/03)
The paper describes a synthetic approach to toddaquinoline, an unusual alkaloid from the root bark of Formosan Toddalia asiatica. Key steps are a cis-selective Wittig coupling and a trialkyltin mediated, intramolecular cyclisation of an aryl radical to C-
Sythesis of 2,2'-Diacyl-1,1'-biaryls. Regiocontrolled Protection of Ketones in Unsymmetrically Substituted 9,10-Phenanthrenequinones
Mervic, Miljenko,Ghera, Eugene
, p. 4720 - 4725 (2007/10/02)
A regiocontrolled monoketalization of unsymmetrically substituted phenanthrenequinones by use of 2,2-dimethyl-1,3-propanediol as the ketalizing reagent has been effected with the help of bromo substitution in one of the aromatic rings at the C-1 or C-8 po
