16721-45-2Relevant articles and documents
Efficient access to novel furanofurone compounds from quinic acid: Studies of inter-and intramolecular Wittig reactions on lactones
Baptistella, Lúcia Helena Brito,Jorge, André De Carvalho
, p. 3045 - 3049 (2007)
(-)-Quinic acid has been converted into derivatives of a furo[3,2-b]furan-2-one system using Wittig olefination reactions of lactones. Studies for this transformation included the use of microwave-assisted reactions. Georg Thieme Verlag Stuttgart.
Novel photocyclization of β,γ-unsaturated oximes
Armesto, Diego,Ramos, Ana,Ortiz, Maria J.,Mancheno, Maria J.,Mayoral, Elena P.
, p. 514 - 516 (1995)
Previously, β,γ-unsaturated oximes were thought to be photochemically unreactive.The present study reports the first three examples of photocyclization of β,γ-unsaturated ketoximes to yield 4,5-dihydroisoxazole derivatives.Typically, acetophenone-sensitiz
Ylide-Stabilized Phosphenium Cations: Impact of the Substitution Pattern on the Coordination Chemistry
Stalder, Tobias,Krischer, Felix,Steinert, Henning,Neigenfind, Philipp,Gessner, Viktoria H.
supporting information, (2022/01/11)
Although N-heterocyclic phosphenium (NHP) cations have received considerable research interest due to their application in organocatalysis, including asymmetric synthesis, phosphenium cations with other substitution patterns have hardly been explored. Her
Asymmetric synthesis and biological evaluation of (+)-cardiobutanolide, (?)-3-deoxycardiobutanolide and analogues as antiproliferative agents
Francuz, Jovana,Jakimov, Dimitar,Popsavin, Mirjana,Popsavin, Velimir,Benedekovi?, Goran,Kesi?, Jelena,Koji?, Vesna,Kova?evi?, Ivana,Rodi?, Marko V.,Zelenovi?, Bojana Sre?o
, (2021/08/30)
Two natural products, (+)-cardiobutanolide and (?)-3-deoxycardiobutanolide, as well as five new analogues, were synthesized in several steps that included zinc-mediated THF ring opening, subsequent stereoselective olefination, and final Sharpless asymmetric dihydroxylation. In vitro antitumour activities of these compounds were evaluated against a panel of eight human tumour cell lines and one normal cell line. Some of compounds displayed powerful effects against tumour cells, but none of them were active toward normal cells. A SAR study revealed that the change of configuration at the C-6 and C-7 position of (+)-cardiobutanolide decreases antitumour activity of analogues. It also appears that the presence of a hydroxyl group at the C-3 position increases the activity of this type of lactones. A comparison of activities of conformationally rigid lactone goniofufurone with that of more flexible cardiobutanolide and 3-deoxycardiobutanolide indicates that steric flexibility has a positive effect on cytotoxicity. It was also confirmed that removal of the phenyl group may result in analogues of higher activity. Flow cytometry analysis revealed that the synthesized compounds did not induce apoptosis and necrosis of K562 cells. However, Western blot analysis showed that all compounds but one had an increased Bax/Bcl-2 protein expression ratio.
Silver-Catalysed Hydroarylation of Highly Substituted Styrenes
Dalton, Toryn,Gre?ies, Steffen,Das, Mowpriya,Niehues, Maximilian,Schrader, Malte L.,Gutheil, Christian,Ravoo, Bart Jan,Glorius, Frank
supporting information, p. 8537 - 8541 (2021/03/16)
Hydroarylation is an effective strategy to rapidly increase the complexity of organic structures by transforming flat alkene moieties into three-dimensional frameworks. Many strategies have already been developed to achieve the hydroarylation of styrenes,
