68382-89-8Relevant articles and documents
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.
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.
