72128-81-5Relevant academic research and scientific papers
A SHORT SYNTHESIS OF γ-HYDROXYCYCLOPENTENONES
Curran, Dennis P.
, p. 3443 - 3446 (1983)
A facile synthesis of γ-hydroxycyclopentenones is described involving olefin-nitrile oxide cycloaddition, isoxazoline reduction, and intramolecular aldol cyclization.Applications toward rethrolones and important prostanoid synthons are presented.
New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity
Chimichi, Stefano,Boccalini, Marco,Cosimelli, Barbara,Dall'Acqua, Francesco,Viola, Giampietro
, p. 5215 - 5223 (2007/10/03)
A convenient route to new 3(2H)-furanones is described through hydrogenolysis and subsequent acidic hydrolysis of isoxazoles. The antiproliferative activity of title compounds were evaluated against leukemia-, carcinoma-, neuroblastoma-, and sarcoma-derived human cell lines in comparison to the natural compound geiparvarin. The structure activity relationship indicated that the maximum in vitro antiproliferative activity correlates with the presence of a heterocyclic ring on the ethenyl moiety.
Nucleophilic Additions to and Reductions of 5-Formyl- and 5-Acyl-2-isoxazolines (4,5-Dihydroisoxazoles): A Stereoselective Route to β,γ-Dihydroxy Ketones
Curran, Dennis P.,Zhang, Jiancun
, p. 2613 - 2625 (2007/10/02)
Reductions of readily available 5-acyl-2-isoxazolines with L-Selectride follow the Felkin-Anh model and produce syn-5-hydroxyalkyl-2-isoxazolines with excellent (>95:5) selectivities.Swern oxidation of 5-hydroxymethyl-2-isoxazolines, followed by direct ad
Silyl Nitronates in Organic Synthesis. Routes to Heterocycles and Cyclopentanoids. Synthesis of Allethrolone and Calythrone. Acylation and Cyanohydroxylation of Double Bonds. An Exploratory Study
Andersen, Soeren H.,Das, Nalin B.,Joergensen, Ruth D.,Kjeldsen, Gunhild,Knudsen, Jes S.,et al.
, p. 1 - 14 (2007/10/02)
Silyl nitronates are versatile reagents for the preparation of heterocycles by dipolar addition to double bonds.The intermediate isoxazolidines can be transformed to 2-isoxazolines, isoxazoles, furans, dihydrofuranones, pyrazoles, pyridazines and pyridazones.Reduction of 2-isoxazolines with Ti3+ leads to hydroxylated 1,4-diketones, which subsequently can be cyclized to cyclopentenones.Routes to calythrone, rethrolones, prostanoids and a number of naturally occurring dihydrofuranones are devised, as well as synthetic procedures for acylation, preparation of endiones, hydroxyacylation, cyanation and hydroxycyanation of double bonds.
