758709-48-7Relevant academic research and scientific papers
Synthesis and structure of bis[1-(1-adamantyl)-4,4,4-trifluorobutane-2,4- dionato]copper
Khamylov,Pochekutova,Petrov,Sizov,Fukin,Kurskii,Arapova
, p. 31 - 36 (2009)
Previously unknown 1-(1-adamantyl)-4,4,4-trifluorobutane-2,4-dione and its copper complex, bis [1-(1-adamantyl)-4,4,4-trifluorobutane-2,4-dionato]copper, were synthesized. The 1H NMR, IR, and ESR spectra and X-ray diffraction patterns of the sy
Exploiting the facile release of trifluoroacetate for the α-methylenation of the sterically hindered carbonyl groups on (+)-sclareolide and (-)-eburnamonine
Riofski, Mark V.,John, Jinu P.,Zheng, Mary M.,Kirshner, Julia,Colby, David A.
experimental part, p. 3676 - 3683 (2011/06/24)
An efficient method for the α-methylenation of carbonyl groups is reported, and this transformation is accomplished by a facile elimination of trifluoroacetate during the formation of the olefin. This method represents an improvement beyond existing protocol in cases of steric hindrance, and we have demonstrated the utility of the process across a series of ketones, lactams, and lactones. Additionally, we have applied this method to produce semisynthetic derivatives of the natural products (+)-sclareolide and (-)-eburnamonine, in which the carbonyl group is proximal to bulky functional groups. Mechanistic insight is also provided from a time course of 19F NMR. Biological evaluation of the natural-product-derived enones led to the identification of a derivative of (-)-eburnamonine with significant cytotoxicity (LC50 = 14.12 ?M) in drug-resistant MDA-MB-231 breast cancer cells.
