58311-18-5

Upstream product

• 126965-33-1 D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid anhydride 
• 4773-01-7 (3R*,4R*)-3-(3,4-dimethoxybenzyl)-4-(3,4-dimethoxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 115754-03-5 4-((E)-3-Bromo-propenyl)-1,2-dimethoxy-benzene 
• 42923-56-8 veratrylidene-succinic acid dimethyl ester 
• 126965-32-0 meso-1,2-bis[(3,4-dimethoxyphenyl)methyl]ethane-1,2-dicarboxylic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 3688-23-1 (-)-secoisolariciresinol 
• 77-78-1 dimethyl sulfate 
• 526-06-7 eudesmin 
• 186581-53-3 diazomethane 
• 157072-28-1 4-O-methyl-3'-O-demethyl-(-)-secoisolariciresinol 
• 25488-59-9 dimethylmatairesinol 
• 135588-81-7 (3R,4R,5R)-3,4-Bis-(3,4-dimethoxy-benzyl)-5-(2-isopropyl-5-methyl-cyclohexyloxy)-dihydro-furan-2-one 
• 60102-89-8 (+)-epipinoresinol dimethyl ether 

Downstream Products

• 5701-82-6 2,3-bis[(3,4-dimethoxyphenyl)methyl]butane 
• 4773-01-7 (3R*,4R*)-3-(3,4-dimethoxybenzyl)-4-(3,4-dimethoxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 62624-76-4 (8R,8'R)-9,9'-epoxy-3,4,3',4'-tetramethoxylignane 
• 119098-90-7 (8R,8R')-3,4,3',4'-tetramethoxylignan-9,9'-diyl bis(methanesulfonate) 
• 119098-89-4 (8R,8'R)-9,9'-dimethylmethylenedioxy-3,4,3',4'-tetramethoxylignane 
• 10351-88-9 phyllanthin 
• 93-07-2 Veratric acid 
• 521-54-0 (7S,8S,8'R)-3,4,3',4'-tetramethoxy-7,6',8,8'-neolignan (-)-galbulin 
• 119030-75-0 Secoisolariciresinol-di-Me-ether-diacetat 
• 10352-26-8 trans-3,4-bis(3,4,-dimethoxybenzyl)tetrahydrofuran 

Relevant academic research and scientific papers

Absolute configuration and anticancer activity of taxiresinol and related lignans of Taxus wallichiana

Absolute configuration of taxiresinol 1, a lignan from the heartwood of Taxus wallichiana has been determined as 8R, 8′R, and 7′R with the help of chemical correlation method and X-ray crystallography. The anticancer activity of taxiresinol 1 and other tw

Synthesis and applications of diphosphine ligands derived from the lignan hydroxymatairesinol

Highly efficient methods for synthetic modifications of the natural lignan hydroxymatairesinol into chiral diphosphines similar to DIOP were developed. Catalytic activity and induction of enantioselectivity for the prepared phosphines were evaluated in rh

Identification of lignans by liquid chromatography-electrospray ionization ion-trap mass spectrometry

The fragmentation pattern of 30 compounds belonging to different classes of the lignan family was studied by liquid chromatography-electrospray ionization ion-trap mass spectrometry. On the basis of the observed fragmentation patterns, identification of d

Short and stereoselective total synthesis of furano lignans (±)-dihydrosesamin, (±)-lariciresinol dimethyl ether, (±)-acuminatin methyl ether, (±)-sanshodiol methyl ether, (±)-lariciresinol, (±)-acuminatin, and (±)-lariciresinol

Intramolecular radical cyclization of suitably substituted epoxy ethers 4a-g using bis(cyclopentadienyl)titanium(III) chloride as the radical source resulted in trisubstituted tetrahydrofurano lignans and 2,6-diaryl-3,7-dioxabicyclo [3.3.0] octane lignans depending on the reaction conditions. The titanium(III) species was prepared in situ from commercially available titanocene dichloride and activated zinc dust in THF. Upon radical cyclization followed by acidic workup, epoxy olefinic ethers 4a-g afforded furano lignans dihydrosesamin 1a, lariciresinol dimethyl ether lb, acuminatin methyl ether le, and sanshodiol methyl ether 1g directly and lariciresinol 1h, acuminatin li, and lariciresinol monomethyl ether 1j after removal of the benzyl protecting group by controlled hydrogenolysis of the corresponding cyclized products. The furofuran lignans sesamin 2a, eudesmin 2b, and piperitol methyl ether 2e were also prepared directly by using the same precursors 4a-f on radical cyclization followed by treatment with iodine and pinoresinol 2h, piperitol 2i, and pinoresinol monomethyl ether 2j after controlled hydrogenolysis of the benzyl protecting group of the corresponding cyclized products. Two naturally occurring acyclic lignans, secoisolariciresinol 5h and secoisolariciresinol dimethyl ether 5b, have also been prepared by exhaustive hydrogenolysis of 2h and 2b, respectively.

Oxidative cyclisation of 3,4-dibenzyltetrahydrofurans using ruthenium tetra(trifluoroacetate)

A series of trans-3,4-dibenzyltetrahydrofurans has been synthesised and subjected to oxidative cyclisation using ruthenium tetra(trifluoroacetate), affording dibenzocyclooctadiene lignans belonging to the isostegane series, in high yields. Since no evidence was found for the formation of the corresponding stegane isomers it is assumed that the reactions proceed with complete diastereoselectivity.

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

Asymmetric Synthesis of Lignans of the Dibenzylbutanediol and Tetrahydrodibenzocyclooctene Series

Enolate anions obtained by conjugate addition to (-)-5-(1-menthyloxy)furan-2(5H)-one are quenched with benzyl bromides or iodides to yield homochiral dibenzylbutyrolactones.Desufurisation followed by lithium aluminium hydride reduction affords homochiral

Asymmetric Syntheses of Lignans of the Dibenzylbutyrolactone, Dibenzylbutanediol, Aryltetralin and Dibenzocyclooctadiene Series

General procedures are outlined for the asymmetric syntheses of ligands of the dibenzylbutyrolactone, dibenzylbutanediol, aryltetralin and dibenzocyclooctadiene series, from tandem addition products derived from 4-mentyloxybutenolide.

LIGNANES.10. PREPARATION DES (R)-(+) ET (S)-(-)-β-PIPERONYL ET β-VERATRYL-γ-BUTYROLACTONES ET LEUR UTILISATION DANS LA SYNTHESE TOTALE DE LIGNANES OPTIQUEMENT ACTIFS

A simple and efficient route leading to optically active β-benzyl-γ-butyrolactones is described.Thus, the methyl (R,S)-α-benzylhemisuccinate resulting from a Stobbe condensation with an appropriate aromatic aldehyde, followed by catalytic hydrogenation of the intermediate α-benzylidene hemisuccinic ester, was resolved by means of a chiral base (ephedrine or α-methyl benzylamine).Reduction of each enantiomer, using calcium borohydride, then led to the corresponding optically active β-benzyl-γ-butyrolactone.In this way, the following two lactones were obtained in both (R)-(+) and (S)-(-) enantiomeric forms, β-piperonyl- and β-veratryl-γ-butyrolactones 1 and 2 respectively.These lactones were used as key-intermediates for the syntheses of 17 optically active lignans and lignoids, such as (-)-dimethylmatairesinol (-)-23, (-)-kusunokinin (-)-26 and (+)-dimethylisolariciresinol (+)-35.