68382-89-8Relevant academic research and scientific papers
Design and synthesis of novel prostaglandin E2 ethanolamide and glycerol ester probes for the putative prostamide receptor(s)
Shelnut, Erin L.,Nikas, Spyros P.,Finnegan, David F.,Chiang, Nan,Serhan, Charles N.,Makriyannis, Alexandros
, p. 1411 - 1415 (2015)
Novel prostaglandin-ethanolamide (PGE2-EA) and glycerol ester (2-PGE2-G) analogs were designed and synthesized to aid in the characterization of a putative prostamide receptor. Our design incorporates the electrophilic isothiocyanato and the photoactivatable azido groups at the terminal tail position of the prototype. Stereoselective Wittig and Horner-Wadsworth-Emmons reactions install the head and the tail moieties of the PGE2 skeleton. The synthesis is completed using Mitsunobu azidation and peptide coupling as the key steps. A chemoenzymatic synthesis for the 2-PGE2-G is described for first time.
Straightforward synthesis of functionalized (E)-3-acylacrylic acids
Sivák, Ivan,Václav, Jakub,Berke?, Du?an,Kolarovi?, Andrej
, p. 8871 - 8875 (2015/11/02)
An experimentally simple, mild and straightforward synthetic route towards diversely functionalized (E)-3-acylacrylic acids is described, with Horner-Wadsworth-Emmons (HWE) reaction as the key step. The substrate scope and limitations of the HWE reaction were investigated with a range of β-ketophosphonates. Glyoxylic acid monohydrate was demonstrated to be fully compatible with the HWE reaction conditions, thus avoiding a troublesome hydrolysis of the corresponding 3-acylacrylates in the last step and providing a valuable synthetic shortcut.
New Syntheses of Some Functionalized and Acetylenic β-Keto Phosphonates
Delamarche, Isabelle,Mosset, Paul
, p. 5453 - 5457 (2007/10/02)
β-Keto phosphonates ω-functionalized by an ester group 1a-f, by a hydroxyl 5, and with a triple bond conjugated to the carbonyl group 2a-c were prepared by reacting dimethyl (lithiomethyl)phosphonate (3) with adequate electrophiles.Cyclic anhydrides such as succinic and glutaric anhydrides were employed for the synthesis of the two first homologs 1a and 1b.To obtain the other longer homologs 1c-f, 3-acylthiazolidine-2-thiones 7a-d easily prepared using cheap 2-mercaptothiazoline proved to be the electrophiles of choice.On the other hand, the synthesis of keto phosphonates 2a-c required the use of N-methoxy-N-methylamides.
