Prostaglandin endoperoxide synthesis

Synthesis of Several Analogs of the Prostaglandin Endoperoxide PGH2... 

The photoinduced-addition of alcohols to cycloalkenones has been investigated by Fraser-Reid and co-workers,4 by Paquette,5 and was used as the key step in the synthesis of the prostaglandin endoperoxide analogue (15S)-hydroxy-9a,11a-epoxymethanoprosta-(52,13E)-dienoic acid,6 and for the recent synthesis of 2, 3 -dideoxy-3 -hydroxymethyl-5 -carbanucleosides.7 No work (other than our own) has been reported on the photoinduced-addition of alcohols to 5-substituted furan-2(5H)-ones. 

Amino-3-fluorobenzoic acid is an important intermediate in the synthesis of derivatives of indole, such as the potent and selective thromboxane/prostaglandin endoperoxide receptor antagonist L-670,596 or the anti-inflammatory agent Etodolac. Compounds of this type have therapeutic applications. 2-Amino-3-fluoro-benzoic add is aiso an important precursor for the synthesis of fluoroacridines, which can be converted to interesting tridentate ligands, such as Acriphos. ... 

Synthesis of prostaglandins and thromboxanes begins with the oxidative cyclization of free arachidonic acid to yield PGH2 by prostaglandin endoperoxide synthase—a microsomal protein that has two catalytic activities fatty acid cyclooxygenase (COX) and peroxidase. There are two isozymes of the synthase COX-1 and COX-2. Leukotrienes are produced by the 5-lipoxygenase pathway. 

Kalgutkar, A. S. Crews, B. C. Mamett, L. J. Design, synthesis, and biochemical evaluation of N-substituted maleimides as inhibitors of prostaglandin endoperoxide synthase. /. Med. Chem. 1996, 39, 1692-1703. 

Coughlin, D.J. and Salomon, R.G. (1977) Synthesis and thermal reactivity of some 2,3-dioxabicyclo[2.2.1]heptane models of prostaglandin endoperoxides. Journal of the American Chemical Society, 99 (2), 655-657. 

Prostaglandin endoperoxide H2 synthase (PGHS) [EC 1.14.99.1] isoenzymes 1 and 2 catalyze the committed step in prostanoid synthesis via two sequential enzymatic reactions... 

An ylide generated from the phosphonium salt (76) with lithium di-isopropyl-amide has been used in the synthesis of the 9,11-aza-analogue of prostaglandin endoperoxide PGHg. ... 

PGs are synthesized in a stepwise manner by microsomal enzymes. The metabolic pathways discussed here use arachidonic acid as an example. Similar pathways are applicable to other polyenoie fatty acids. PG synthesis is started by microsomal prostaglandin endoperoxide... 

Prostacyclins and thromboxanes, synthesis of 84S449 79T2705. Prostaglandin endoperoxides, thromboxanes, prostacyclins, synthesis and... 

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