160425-72-9

Upstream product

• 14032-72-5 5-oxo-2,5-dihydrofuran-2-yl acetate 
• 14032-66-7 5-hydroxy-2-(5H)-furanone 
• 108-24-7 acetic anhydride 
• 108-05-4 vinyl acetate 

Relevant academic research and scientific papers

Synthesis and pharmacological characterisation of arctigenin analogues as antagonists of AMPA and kainate receptors

(-)-Arctigenin and a series of new analogues have been synthesised and then tested for their potential as AMPA and kainate receptor antagonists of human homomeric GluA1 and GluK2 receptors expressed in HEK293 cells using a Ca2+ influx assay. In general, these compounds showed antagonist activity at both receptors with greater activity evident at AMPARs. Schild analysis indicates that a spirocyclic analogue 6c acts as a non-competitive antagonist. Molecular docking studies in which 6c was docked into the X-ray crystal structure of the GluA2 tetramer suggest that (-)-arctigenin and its analogues bind in the transmembrane domain in a similar manner to the known AMPA receptor non-competitive antagonists GYKI53655 and the antiepileptic drug perampanel. The arctigenin derivatives described herein may serve as novel leads for the development of drugs for the treatment of epilepsy. This journal is

GRACILIN A AND CONGENERS AS IMMUNOSUPPRESSIVE AND NEUROPROTECTIVE AGENTS

Gracilin A congeners and methods for their use as immunosuppressive and neuroprotective agents.

Enzymatic synthesis of optically active lactones via asymmetric bioreduction using ene-reductases from the old yellow enzyme family

In contrast to the widely studied asymmetric bioreduction of α,β-unsaturated carboxylic acid esters catalyzed by ene-reductases, the reaction applied to lactones remains unexplored. A broad set of ene-reductases was found to reduce various α-, β- and γ-substituted α,β-unsaturated butyrolactones to yield the corresponding saturated non-racemic lactones. Substitution patterns greatly influenced activities and stereoselectivities and lactone products were obtained in moderate to excellent yields; importantly, enzyme-based stereocontrol allowed access to both enantiomers in up to >99% ee. Chiral recognition of a distant γ-center led to kinetic resolution with remarkable enantioselectivities (E values up to 49). An unprecedented case of dynamic kinetic resolution was observed with 3-methyl-5-phenylfuran-2(5H)-one, whereby spontaneous racemization of the substrate furnished the product in up to 73% conversion and >99% ee and 96% de.

Stereocontrolled total synthesis of (-)-kainic acid. Regio- and stereoselective lithiation of pyrrolidine ring with the (+)-sparteine surrogate

(Chemical Equation Presented) A stereocontrolled total synthesis of (-)-kainic acid is described. cis-3,4-Disubstituted pyrrolidine ring was constructed by [3 + 2] cycloaddition of azomethine ylide with chiral butenolide. The crucial introduction of carboxyl group at the C-2 position was executed by regio- and stereoselective lithiation of the pyrrolidine ring in the presence of a (+)-sparteine surrogate followed by trapping with carbon dioxide.

Lipase-catalyzed second-order asymmetric transformations as resolution and synthesis strategies for chiral 5-(acyloxy)-2(5H)-furanone and pyrrolinone synthons

By use of lipase R (Amano, Penicillium roqueforti) immobilized on Hyflo Super Cell it is possible to convert at ambient temperature 5-hydroxy-5H-furan-2-one (5) to acetic acid 5-oxo-2,5-dihydrofuran-2-yl ester (1b) by acylation with vinyl acetate in 1:1 cyclohexane-butyl acetate. At 90% conversion the enantiomeric excess of 1b is 100%. This is an example of an enzyme-catalyzed second-order transformation whereby the unreactive enantiomer of 5 racemizes during reaction, allowing up to 100% conversion and obtainment of high enantiomeric excesses. The method is even more effective with 5-(acyloxy)-2(5H)-pyrrolinones. Racemic acetic acid 1-acetyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester (2) when treated with the lipase from Candida antarctica at ambient temperature in 3:1 n-hexane-butanol undergoes exactly 50% conversion to afford (+)-2 in >99% enantiomeric excess. This is the unreactive enantiomer. The (-)-enantiomer is converted to the 5-hydroxy derivative 6, which with Candida antarctica in 1:1 n-hexane-vinyl acetate at 69°C (the temperature is higher to increase the rate of racemization) is transformed (100% conversion) to (-)-2, obtained in >99% enantiomeric excess. The scope of these second-order asymmetric transformations is discussed as well as procedures for optimalization of reaction conditions whereby transesterification strategies are combined with those of second-order asymmetric transformation.

Lipase catalyzed enantioselective transesterification of 5-Acyloxy-2(5H)-furanones

Several lipases catalyse the transesterification of γ-acyloxyfuranones in organic solvents with high enantioselectivities. This method has been used for the kinetic resolution of 5-acetoxy-2(5H)-furanone, 5-acetoxy-4-methyl-2(5H)-furanone and 5-propionyloxy-2(5H)-furanone, in e.e.'s ranging from 68-98%.