833-38-5Relevant academic research and scientific papers
Diels-Alder/thiol-olefin co-oxygenation approach to antimalarials incorporating the 2,3-dioxabicyclo[3.3.1]nonane pharmacophore
O'Neill, Paul M.,Verissimo, Edite,Ward, Stephen A.,Davies, Jill,Korshin, Edward E.,Araujo, Nuna,Pugh, Matthew D.,Cristiano, M. Lurdes S.,Stocks, Paul A.,Bachi, Mario D.
, p. 2991 - 2995 (2008/09/20)
A Diels-Alder/thiol-olefin co-oxygenation approach to the synthesis of novel bicyclic endoperoxides 17a-22b is reported. Some of these endoperoxides (e.g., 17b, 19b, 22a and 22b) have potent nanomolar in vitro antimalarial activity equivalent to that of the synthetic antimalarial agent arteflene. Iron(II)-mediated degradation of sulfone-endoperoxide 19b and spin-trapping with TEMPO provide a spin-trapped adduct 25 indicative of the formation of a secondary carbon centered radical species 24. Reactive C-radical intermediates of this type may be involved in the expression of the antimalarial effect of these bicyclic endoperoxides.
Ring enlargement reaction of 2-(1-alkenyl)-1-cyclobutyl ketones. A new method for the preparation of 4-acyl-1-cyclohexenes
Fujiwara, Tooru,Takeda, Takeshi
, p. 6027 - 6030 (2007/10/02)
Various 1,2-disubstituted 4-acyl-1-cyclohexenes were obtained by the ethylaluminum dichloride promoted ring enlargement reaction of 2-(1-alkenyl)-1-cyclobutyl ketones prepared by the conjugate addition of 1-alkenylmagnesium bromides With 1-cyclobutenyl ketones.
