76436-47-0Relevant academic research and scientific papers
A micromethod for the determination of the absolute stereochemistry at C-15 of prostanoids and related compounds
Just, George,Oh, Hunseung
, p. 3667 - 3668 (1980)
Reductive ozonolysis of Δ13-15-acetoxy prostanoids, followed by reaction of the resulting 2-acetoxyheptanal with l-ephedrine, gives oxazolidines whose R, values on t.l.c. are characteristic of the chirality of the acetoxy group, thus permitting the determination of the absolute stereochemistry at a 5 μg level.
Formation of Isoxazolyl Hydroperoxides via a Novel Oxidative Fragmentation of Bicyclic Isoxazolidines
Bundy, Gordon L.,Baldwin, J. Marvin,Peterson, David C.
, p. 976 - 982 (2007/10/02)
(5Z,9α,11α,13E)-9,11-(Epoxyimino)prosta-5,13-dienoic acid (2) and the corresponding methyl ester 3 undergo a novel oxidative fragmentation reaction in the presence of air.The resulting four isomeric isoxazolyl hydroperoxides 4a,b and 5a,b formed cleanly in similar amounts and in good combined yield, have been characterized spectrally and by further chemical transformations.The novel oxidative fragmentation reaction is very facile with the strained bicyclic isoxazolidine ring system (e.g.,3) but occurs (more slowly) in less constrained substrates as well.The new isoxazolyl hydroperoxides, as well as the corresponding alcohols an ketones, are potent inhibitors of PGH2-induced human platelet aggregation.
