77756-19-5

Upstream product

• 77756-18-4 (R)-3-Hydroxymethyl-4-(3-methoxy-phenyl)-butyric acid 
• 141737-57-7 (R)-N-benzyl-4-hydroxy-3-(3-methoxyphenyl)methylbutanamide 
• 171007-72-0 3-(m-Methoxyphenyl)prop-1-yl diazoacetate 
• 229017-00-9 4-acetoxy-3-(3-methoxybenzyl)butyronitrile 
• 263716-58-1 ethoxycarbonyl-(2R)-(carboxymethyl)-3-(3'-methoxyphenyl)propionic acid 
• 725724-51-6 (R)-3-(3-Methoxy-benzyl)-dihydro-furan-2,5-dione 
• 690631-39-1 3-(tert-butoxycarbonyl)-4-[(3-methoxyphenyl)methyl]-dihydro-2(3H)-furanone 
• 24743-14-4 1-allyl-3-methoxybenzene 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 690631-43-7 [(E)-(R)-1-Hydroxy-4-(3-methoxy-phenyl)-but-2-enyl]-phosphonic acid dimethyl ester 
• 690631-42-6 (1R)(2E) dimethyl [1-(methoxycarbonyloxy)-4-(3-methoxyphenyl)-2-butenyl] phosphonate 
• 690631-47-1 2-[(E)-(R)-3-(Dimethoxy-phosphoryl)-1-(3-methoxy-benzyl)-allyl]-malonic acid tert-butyl ester methyl ester 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 338945-89-4 (2R)-2-(3-methoxybenzyl)succinic acid 

Downstream Products

• 80704-91-2 (3R,4R)-3,4-bis<(3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 76543-15-2 (-)-enterolactone 

Relevant academic research and scientific papers

Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters

In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate α-borylzinc reagent are probed and the synthetic utility of the products is demonstrated by application to the synthesis of (-)-aphanorphine and (-)-enterolactone.

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

First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer–Villiger monooxygenases

Abstract: This study investigates the substrate profile of cycloalkanone monooxygenase and 2-oxo-Δ3-4,5,5-trimethylcyclopentenylacetyl-coenzyme A monooxygenase, two recently discovered enzymes of the Baeyer–Villiger monooxygenase family, used as whole-cell biocatalysts. Biooxidations of a diverse set of ketones were performed on analytical scale: desymmetrization of substituted prochiral cyclobutanones and cyclohexanones, regiodivergent oxidation of terpenones and bicyclic ketones, as well as kinetic resolution of racemic cycloketones. We demonstrated the applicability of the title enzymes in the enantioselective synthesis of (R)-(?)-Taniguchi lactone, a building block for the preparation of various natural product analogs such as ent-quinine. Graphical abstract: [Figure not available: see fulltext.]

Organocatalytic Enantioselective Alkylation of Aldehydes with [Fe(bpy)3]Br2 Catalyst and Visible Light

Catalytic amounts (2.5 mol %) of [Fe(bpy)3]Br2 complex in the presence of visible light and the MacMillan catalyst 3 (20 mol %) are highly effective in promoting an enantioselective organocatalytic photoredox alkylation of aldehydes

γ-Selective directed catalytic asymmetric hydroboration of 1,1-disubstituted alkenes

Directed catalytic asymmetric hydroborations of 1,1-disubstituted alkenes afford γ-dioxaborato amides and esters in high enantiomeric purity (90-95% ee). The Royal Society of Chemistry 2012..

Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones

Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.

Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones

Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.

An access to chiral β-benzyl-γ-butyrolactones and its application to the synthesis of enantiopure (+)-secoisolariciresinol, (-)-secoisolariciresinol, and (-)-enterolactone

Both enantiomers of secoisolariciresinol and enantiopure (-)-enterolactone were synthesized through a highly stereoselective convergent synthesis. An Evans diastereoselective alkylation followed by a substrate-induced diastereoselective -alkylation of the newly formed optically active β-benzyl-γ- butyrolactone gave the β-β′ linkage of the target skeleton. The (S,S)- and (R,R)-enantiomers of secoisolariciresinol and (-)-enterolactone were obtained in 12-14% (11 steps) and 20% (7 steps) overall yield, respectively. Georg Thieme Verlag Stuttgart New York.

Asymmetric syntheses of (-)-enterolactone and 7′R)-7′- hydroxyenterolactone via organocatalyzed aldol reaction

(Chemical Equation Presented) Short syntheses of (-)-enterolactone (1a) and (7′R)-7′-hydroxyenterolactone (1b) have been achieved utilizing organocatalyzed asymmetric cross-aldol reaction of aldehydes 2 and 3 and base-mediated alkylation of lactones 5 and 4.