Iron- or silver-catalyzed oxidative fluorination of cyclopropanols for the synthesis of β-fluoroketones
The FeIII- or AgI-catalyzed oxidative fluorination of cyclopropanols via radical rearrangement is disclosed. This process features a straightforward and highly effective protocol for the site-specific synthesis of β-fluoroketones and represents an expedient method for the synthesis of γ-, δ- and ε-fluoroketones. Notably, this reaction proceeds at room temperature and tolerates a diverse array of cyclopropanols.
Ren, Shichao,Feng, Chao,Loh, Teck-Peng
supporting information
p. 5105 - 5109
(2015/05/13)
Optimisation of the allylsilane approach to C-10 deoxo carba analogues of dihydroartemisinin: Synthesis and in vitro antimalarial activity of new, metabolically stable C-10 analogues
An optimised protocol has been developed for the coupling of dihydroartemisinin benzoate with a range of aromatic allylsilanes to provide a number of new C-10 deoxo derivatives (11a-11g) in yields ranging from 70 to 94%. These compounds were up to ten times more potent than artemisinin in in vitro tests against the chloroquine resistant K1 strain of Plasmodium falciparum. Ferrous mediated degradation of these analogues produces as the main product, a dicarbonyl formate 12, which is not seen when the same reaction is carried out with artemisinin or artemether. This finding may indicate that analogues in this class have a subtly different "antimalarial" mechanism of action.
O'Neill,Pugh,Stachulski,Ward,Davies,Kevin Park
p. 2682 - 2689
(2007/10/03)
A Topliss tree analysis of the HIV-protease inhibitory activity of 6- phenyl-4-hydroxy-pyran-2-ones
In a study of 4-hydroxy-pyran-2-ones as possible inhibitors of HIV protease, a series of compounds were synthesized following the Topliss operational scheme for substitution on a phenyl group at the 6 position of the pyrone. In addition, a number of compounds with polar substituents were made.