4718-24-5

Upstream product

• 150132-92-6 (+)-picrodimethylretrodendrin 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 103477-59-4 6-(3,4-dimethoxybenzyl)veratraldehyde 
• 103477-60-7 1-(3,4-dimethoxyphenyl)-3-hydroxy-5,6-dimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide 
• 72430-92-3 4-[(3,4-dimethoxyphenyl)methyl]dihydrofuran-2-one 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 115061-18-2 (E)-3-(methoxycarbonyl)-4-(3,4-dimethoxyphe-nyl)but-3-enoic acid 
• 78647-52-6 (+/-)-4-(3,4-dimethoxyphenyl)-3-methoxycarbonylbutanoic acid 
• 78173-81-6 <(dimethoxy-3,4 phenyl)hydroxymethyl>-2 (dimethoxy-3,4 benzyl)-3 butanolide-4 
• 108102-77-8 (R)-4-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one 
• 149143-83-9 α-(3,4-dimethoxyphenyl)-6-bromoveratryl alcohol 
• 2898-57-9 1-bromo-2-(3,4-dimethoxybenzyl)-4,5-dimethoxybenzene 
• 108102-81-4 (-)-(3S,4R,6R)-3-(3',4'-dimethoxy-α-hydroxybenzyl)-4-<3'',4''-dimethoxybenzyl>butyrolactone 
• 78173-81-6 (3S,4R)-4-(3,4-Dimethoxy-benzyl)-3-[(3,4-dimethoxy-phenyl)-hydroxy-methyl]-dihydro-furan-2-one 

Downstream Products

• 78178-27-5 methyl α-retrodendrate dimethyl ether 
• 21966-92-7 isolariciresinol dimethyl ether 
• 78178-25-3 α-retrodendric acid dimethyl ether 
• 6258-39-5 9-(3,4-Dimethoxyphenyl)-6,7-dimethoxynaphtho<2,3-c>furan-1(3H)-one 
• 61248-24-6 r-1-(3,4-dimethoxyphenyl)-t-2,c-3-bis(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products

We disclose a (terpy)NiBr2-catalyzed reaction protocol that regioselectively difunctionalizes unactivated olefins with tethered alkyl halides and arylzinc reagents. The reaction shows an excellent functional group tolerance (such as ketones, es

Asymmetric Synthesis of Dibenzylbutyrolactones and Aryltetralin Lignan Lactones by Tandem Cojugate Addition to a Chiral Butenolide

Addition of sulfur-stabilised carbanions to (-)-5-(1-menthyloxy)furan-2(5H)-one followed by reaction with an aromatic aldehyde affords a short synthesis of enantiomerically pure dibenzylbutyrolactone derivatives.Desulfurisation with NaBH4/NiCl2 proceeds in almost quantitative yield, and reduction with NaBH4/KOH gives the parent dibenzylbutyrolactones including (-)-6-epi-podorhizol.These undergo cyclisation with acid to give homochiral aryltetralines including (-)-deoxyisopodophyllotoxin in high yield.

A General Asymmetric Synthesis of (-)-α-Dimethylretrodendrin and Its Diastereomers

A Diels-Alder cycloaddition between the fumarate of methyl (R)-mandelate 14 and α-hydroxy-α'-aryl-o-quinodimethane 12 produced an exo cycloadduct 15 in 44percent yield which was converted to optically pure (-)-α-dimethylretrodendrin (21) and three of its

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.

A Common Synthetic Route to the Pericarbonyl and Perimethylene Lignan Lactones Dimethyl Conidendrin and Dimethyl Retrodendrin

An all trans 1-aryl-2-methoxycarbonyl tetralin-3-carboxylic acid synthesised in 32percent overall yield can be converted, at will, to either dimethyl conidendrin or dimethyl retrodendrin in one step.

(R)-(+)-β-VERATRYL-γ-BUTYROLACTONE, A NEW KEY-INTERMEDIATE FOR THE ASYMMETRIC SYNTHESIS OF VARIOUS LIGNANS

Methyl α-veratrylhemisuccinate was resolved into its (R)-(+) and (S)-(-) antipodes by (S)-(-) and (R)-(+)-α-methylbenzylamine respectively.Calcium borohydride reduction of the (R)-(+)-hemiester afforded (R)-(+)-β-veratryl-γ-butyrolactone.The latter was us

STRUCTURE AND SYNTHESYS OF HYPOPHYLLANTHIN, NIRTETRALIN, PHYLTETRALIN AND LINTETRALIN

Structures propounded for the four aryltetralin lignan constituents isolated from Phyllanthus niruri Linn. are confirmed by syntheses of their (+/-)-forms.

Synthesis of Aryltetralin and Dibenzylbutyrolactone Lignans: (+/-)-Lintetralin, (+/-)-Phyltetralin, and (+/-)-Kusunokinin

Application of a general synthetic pathway for aryltetralin and dibenzylbutyrolactone lignans, starting from the lithium enolate of 3-(3,4-dimethoxybenzyl)butyrolactone (1) led to syntheses of (+/-)-lintetralin (4), (+/-)-phyltetralin (5), (+/-)-isogalcat