125304-91-8Relevant academic research and scientific papers
Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps
Jagtap, Pratap R.,Císa?ová, Ivana,Jahn, Ullrich
supporting information, p. 750 - 755 (2018/02/09)
A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.
Oxovanadium(v)-induced diastereoselective oxidative homocoupling of boron enolates
Amaya, Toru,Masuda, Takaya,Maegawa, Yusuke,Hirao, Toshikazu
supporting information, p. 2279 - 2281 (2014/03/21)
Oxovanadium(v)-induced dl-selective oxidative coupling of (Z)-boron enolate was demonstrated to give the corresponding 2,3-disubstituted 1,4-diketone in a good yield. High selectivity (up to 94:6) was attained when the reaction was performed with VO(OPr-i)2Cl at -30 °C. The Royal Society of Chemistry 2014.
Medicinal Plants of Southern Africa. Part 4. Synthesis of Brackenin-like Molecules from 1,4-Dicarbonyl Precursors and by Oxydative Coupling. X-Ray Molecular Structure of Racemic-2,3-Dibenzyl-1,4-diphenylbutane-1,4-dione
Drewes, Siegfried E.,Hogan, Craig J.,Kaye, Perry T.,Roos, Gregory H. P.
, p. 1585 - 1591 (2007/10/02)
Oxidative coupling of appropriate trimethylsilyl enol ethers is shown to give 1,4-diaryl-1,4-diketones in acceptable yields.Subsequent dibenzylation of these intermediates affords compounds related to the naturally occuring brackenin (1).Examination of these products by 1H n.m.r. and 13C n.m.r. demonstrates that these techniques can be used for the determination of relative configurations without resorting to X-ray crystallography.
