Synonyms:Prostaglandin;Prostaglandins;Prostanoid;Prostanoids
There total 1 articles about Prostaglandin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
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The research aims to achieve the total synthesis of prostaglandin F2a (PGF2a) using a nickel-promoted cyclization method. The study employs key chemicals such as 1,3-cyclohexadiene (1,3-CHD), hydride nickel complex generated from Ni(acac)2 and PPh3, and various reagents like DIBAL-H, PCC, and Wittig reagents. The researchers successfully synthesized PGF2a by first preparing an optically active substrate (16) from chiral epoxy alcohol (10). This substrate underwent nickel-promoted cyclization in the presence of 1,3-CHD to stereoselectively form the key intermediate (18), which contains the a-chain and four contiguous chiral carbon centers of PGF2a. The intermediate was then transformed into PGF2a through a series of reactions. The study concludes that nickel-promoted cyclization is a promising method for constructing cyclopentanoids and provides a new approach for the synthesis of PGF2a, with further studies ongoing to explore its potential.
The research focuses on a simple total synthesis of prostaglandins, specifically PGF2α, from 4-cumyloxy-2-cyclopentenone, utilizing a synthetic route that involves the key intermediate 2-methylene cyclopentanone. The purpose of this study was to demonstrate the effectiveness of monomeric formaldehyde in trapping kinetic enolates, which are known to be challenging to alkylate. The researchers successfully completed the synthesis in eight steps, yielding (+)-PGF2α and its 15-epimer in an overall 17% yield. The chemicals used in the process include 4-cumyloxy-2-cyclopentenone, (+)-1-iodo-1-octen-3-ol, benzyl chloromethyl ether, tert-butyllithium, tributylphosphine-copper iodide, and formaldehyde, among others. The study concluded that formaldehyde is a valuable trapping agent for certain enolates, and the synthesis described is a relatively simple and convergent method for producing prostaglandins.
The research aimed to discover novel microsomal prostaglandin E2 synthase-1 (mPGES-1) inhibitors that could potentially alleviate inflammatory symptoms by reducing PGE2 levels. The study sought to overcome the synthetic and metabolic drawbacks of N-carboxy-phenylsulfonyl hydrazide (scaffold A) derivatives by exploring N-carboxy-phenylsulfonamide (scaffold B) and N-amido-phenylsulfonamide (scaffold C) as bioisosteric replacements. Among the tested compounds, MPO-0186 (scaffold C) emerged as a potent mPGES-1 inhibitor, showing greater potency than the reference inhibitor MK-886.
The research focuses on the stereoselective synthesis of an important prostaglandin synthetic intermediate, specifically the compound 1. The study explores methods to achieve high diastereoselectivity in the reduction of an allylic alcohol without using expensive reagents or extremely low temperatures. Key chemicals involved in the research include lactone benzoate 2', bromide 3, iodide 4, vinylstannane 6, organocuprate reagent 7, allylic alcohol 9, and the desired intermediate 1. The process involves several steps, such as bromination, iodination, coupling reactions, and stereoselective epoxidation using the Sharpless method. The final isomerization of compound 11 to the target compound 1 is achieved through a three-step procedure involving regioselective opening of the epoxide, oxidation, and thermolysis. The research highlights the potential for significant scale-up of this procedure for preparing diastereomerically pure lactones without the need for tedious chromatography or expensive reagents.
The study investigates the reaction of malonaldehyde with nucleic acids, specifically focusing on the formation of pyrimido[1,2-a]purin-10(3H)-one nucleoside (3) through the thermal decomposition of diastereomers containing oxadiazabicyclononene residues linked to guanosine. Malonaldehyde, a product of lipid peroxidation and prostaglandin biosynthesis, is known for its mutagenic and carcinogenic properties. In this research, guanosine reacts with 1,1,3,3-tetraethoxypropane, which acts as a generator of malonaldehyde, under strongly acidic conditions to form diastereomers 4a and 4b. These diastereomers are then decomposed by heat, yielding the desired pyrimido[1,2-a]purin-10(3H)-one nucleoside (3) in a good yield. The study also proposes a convenient method for the preparation of compound 3, which includes the thermal decomposition process of the diastereomers. The findings suggest that this method is rapid and effective, significantly improving the yield of compound 3 compared to previous methods.
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