255381-83-0Relevant academic research and scientific papers
Cyclopropenones for Metabolic Targeting and Sequential Bioorthogonal Labeling
Row, R. David,Shih, Hui-Wen,Alexander, Austin T.,Mehl, Ryan A.,Prescher, Jennifer A.
, p. 7370 - 7375 (2017)
Cyclopropenones are attractive motifs for bioorthogonal chemistry, owing to their small size and unique modes of reactivity. Unfortunately, the fastest-reacting cyclopropenones are insufficiently stable for routine intracellular use. Here we report cyclop
Synthesis of ω-and (ω - 1)-acetylenic acids from five-, six-, or seven-membered cycloalkanones
Starostin,Ignatenko,Lapitskaya,Pivnitsky,Nikishin
, p. 833 - 837 (2001)
A convenient method for the synthesis of ω-and (ω - 1)-acetylenic acids involves free-radical oxidative scission of cycloalkanones containing five-, six, or seven-membered cycles to give the corresponding ω-olefinic acids followed by bromination of the latter and subsequent dehydrobromination under the action of alkalis.
Ligand-Enabled, Copper-Catalyzed Regio- and Stereoselective Synthesis of Trialkylsubstituted Alkenylboronates from Unactivated Internal Alkynes
Itoh, Taisuke,Shimizu, Yohei,Kanai, Motomu
supporting information, p. 7528 - 7531 (2016/07/06)
We report the first copper-catalyzed regio- and stereoselective borylalkylation of dialkylsubstituted internal alkynes with bis(pinacolato)diboron and alkyl halides. A catalytically generated borylcopper species containing a novel π-accepting N-heterocycl
Gold(I)-Catalysed Cyclisation of Alkynoic Acids: Towards an Efficient and Eco-Friendly Synthesis of γ-, δ- and ?-Lactones
Gasperini, Danila,Maggi, Lorenzo,Dupuy, Stéphanie,Veenboer, Richard M. P.,Cordes, David B.,Slawin, Alexandra M. Z.,Nolan, Steven P.
supporting information, p. 3857 - 3862 (2016/12/16)
The improved synthesis of γ-, δ- and ?-lactones using a dinuclear N-heterocyclic carbene (NHC)-gold(I) catalyst is reported. This solvent-free process provides access to γ- and δ-lactones in high regio- and stereoselectivity. Reactions were performed at l
Oxygenated Metabolites of n-3 polyunsaturated fatty acids as potential oxidative stress biomarkers: Total synthesis of 8-F3t-IsoP, 10-F 4t-NeuroP and [D4]-10-F4t-NeuroP
Guy, Alexandre,Oger, Camille,Heppekausen, Johannes,Signorini, Cinzia,Defelice, Claudio,Fuerstner, Alois,Durand, Thierry,Galano, Jean-Marie
supporting information, p. 6374 - 6380 (2014/06/09)
A wide variety of metabolic products of polyunsaturated fatty acids is of paramount importance for improving our medical knowledge in the field of oxidized lipids. Two novel metabolites of n-3 polyunsaturated fatty acids, 8-F3t-IsoP and 10-F4t-NeuroP as well as a deuterated derivative thereof were synthesized based on an acetylenic intermediate. An original approach achieved lateral chain insertion of 8-F3t-IsoP by a ring-closing alkyne metathesis/semi-reduction strategy together with a temporary tether. Three for the price of one! Two strategies, Caruso coupling or ring-closing alkyne metathesis (RCAM), enabled the synthesis of 8-F 3t-IsoP and 10-F4t-NeuroP and its deuterated derivative from acetylenic intermediateA (see scheme). Such compounds represent potential biomarkers of neuronal oxidative stress.
