80704-91-2

Upstream product

• 26905-40-8 3-methoxybenzylmagnesium chloride 
• 77756-19-5 (R)-4-<(3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 
• 86653-16-9 4-<(3-methoxyphenyl)methyl>dihydrofuran-2(3H)-one 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 591-31-1 3-methoxy-benzaldehyde 
• 10516-71-9 3-(3-Methoxy-phenyl)-propionic acid 
• 6099-04-3 3-methoxycinnamic acid 
• 93578-36-0 1,2-bis[(3-methoxyphenyl)methyl]ethane-1,2-dicarboxylic acid 
• 90110-63-7 3-methoxybenzyl iodide 
• 77756-14-0 Toluene-4-sulfonic acid 2-hydroxymethyl-3-(3-methoxy-phenyl)-propyl ester 
• 77756-15-1 3-Hydroxymethyl-4-(3-methoxy-phenyl)-butyronitrile 
• 77756-13-9 2-<(3-methoxyphenyl)methyl>-1,3-propanediol 
• 61227-48-3 [(3-methoxyphenyl)methyl]propanedioic acid diethyl ester 
• 78473-65-1 C₂₀H₁₇OS₂^(1-) 

Downstream Products

• 76543-15-2 (-)-enterolactone 
• 76543-15-2 (3S,4R)-3,4-Bis-(3-hydroxy-benzyl)-dihydro-furan-2-one 
• 76543-15-2 trans-2,3-bis[(3-hydroxyphenyl)methyl]-γ-butyrolactone 
• 77756-17-3 2,3-bis(3-methoxybenzyl)-4-butanolide 
• 138306-21-5 trans-3,4-bis(3-methoxybenzyl)tetrahydrofuran 
• 76543-16-3 2,3-bis(3-hydroxybenzyl)-butane-1,4-diol 
• 77756-23-1 Meso-2,3-bis-[(3-hydroxyphenyl)methyl]-1,4-butane diol 

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.

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.

Synthesis of (-)-matairesinol, (-)-enterolactone, and (-)-enterodiol from the natural lignan hydroxymatairesinol.

[reaction: see text] We describe here a four-step semisynthetic method for the preparation of enantiomerically pure (-)-enterolactone starting from the readily available lignan hydroxymatairesinol from Norway spruce (Picea abies). Hydroxymatairesinol was

Free-radical-mediated conjugate additions. Enantioselective synthesis of butyrolactone natural products: (-)-Enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid

Lewis acid-mediated conjugate addition of alkyl radicals to a differentially protected fumarate 10 produced the monoalkylated succinates with high chemical efficiency and excellent stereoselectivity. A subsequent alkylation or an aldol reaction furnished the disubstituted succinates with syn configuration. The chiral auxiliary, 4-diphenylmethyl-2-oxazolidinone, controlled the stereoselectivity in both steps. Manipulation of the disubstituted succinates obtained by alkylation furnished the natural products (-)-enterolactone, (-)-arctigenin, and (-)-isoarctigenin. The overall yields for the target natural products were 20-26% over six steps. Selective functionalization of the disubstituted succinates obtained by aldol condensation gave the paraconic acid natural products (-)-nephrosteranic acid (8) and (-)-roccellaric acid (9). The overall yield of the natural products 8 and 9 over four steps was 53% and 42%, respectively.

A short synthesis of biologically active lignan analogues

β-Benzyl-γ-butyrolactones were synthesized in four transition metal catalysed reactions from butynediol, and alkylated to afford new, biologically active lignan analogues.

A short synthesis of both enantiomers of enterolactone

A short and efficient synthesis of both enantiomers of enterolactone, a mammalian lignan, is described. The overall yield for the natural enterolactone, over seven steps, was 19% and for its enantiomer 27%.

Oxidative Homocoupling of Chiral 3-Arylpropanoic Acid Derivatives. Application to Asymmetric Synthesis of Lignans

The oxidative homocouplings of lithium enolates of (4S)-3-(3-arylpropanoyl)-4-isopropyl-2-oxazolidinones and (4R,5S)-1-(3-arylpropanoyl)-3,4-dimethyl-5-phenyl-2-imidazolidinones gave the corresponding R,R-dimers stereoselectively with TiCl4, Ph

Chemoenzymatic enantioselective synthesis of (-)-enterolactone

Enterolactone, a lignan isolated from biological fluids of animals and humans, was synthesized via enzymatic desymmetrization of 2-(3-methoxybenzyl)-1,3-propanediol.

Intramolecular regioselective insertion into unactivated prochiral carbon-hydrogen bonds with diazoacetates of primary alcohols catalyzed by chiral dirhodium(II) carboxamidates. Highly enantioselective total synthesis of natural lignan lactones

Intramolecular insertion into unactivated prochiral C-H bonds of 3-aryl-1-propyl diazoacetates catalyzed by dirhodium(II) tetrakis[methyl 1-(3-phenyl propanoyl)imidazolidin-2-one-4(R or S)-carboxylate], Rh2(4R-MPPIM)4 or Rh2(4S-MPPIM)4, occurs in 91-96% ee and with virtually complete regiocontrol for the formation of β-benzyl-γ-butyrolactones. This methodology has been applied to the total synthesis of dibenzylbutyrolactone lignans (-)- and (+)-enterolactone, (-)- and (+)-hinokinin, and (+)-arctigenin from substituted cinnamic acids in 19-27% overall yields. Aryltetralin lignan (+)-isodeoxypodophyllotoxin was prepared from the reactant 3,4-(methylenedioxy)cinnamic acid in 36% yield overall, and the lactone precursor to (+)-isolauricerisinol was formed in 96.5% ee and 23% yield overall. Applications of the chiral Rh2(MPPIM)4 catalysts to fully aliphatic systems resulting in the formation of β-substituted-γ-butyrolactones with high regiocontrol and with 93-96% ee have demonstrated the generality of this methodology. A model that provides accurate predictions of β-substituted-γ-butyrolactone absolute configurations in these asymmetric metal carbene transformations is described.