82837-97-6

Upstream product

• 186581-53-3 diazomethane 
• 82792-82-3 1-(3,4-Dimethoxy-phenyl)-5,6-dimethoxy-1,3-dihydro-benzo[c]thiophene 2,2-dioxide 
• 624-49-7 dimethylfumarate 
• 5396-64-5 methyl (E)-3-(3,4-dimethoxyphenyl)acrylate 
• 82792-88-9 (2-bromo-4,5-dimethoxyphenyl)methanethiol 
• 54370-00-2 2-bromo-4,5-dimethoxybenzyl alcohol 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 103477-65-2 (1S,2R,3S,4S)-1-(3,4-Dimethoxy-phenyl)-4,6,7-trimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester 
• 82792-86-7 1-(3,4-Dimethoxy-phenyl)-5,6-dimethoxy-1,3-dihydro-benzo[c]thiophene 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 103477-62-9 cis-1-(3,4-dimethoxyphenyl)-3,5,6-trimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide 
• 103477-60-7 1-(3,4-dimethoxyphenyl)-3-hydroxy-5,6-dimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide 
• 103477-67-4 6-(3,4-dimethoxybenzyl)veratrldehyde ethylene glycol acetal 
• 103477-59-4 6-(3,4-dimethoxybenzyl)veratraldehyde 

Downstream Products

• 50656-79-6 (+/-)-phyltetralin 
• 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

Studies on acidic dimerization of 3,4-dioxygenated cinnamate or 1- phenylpropene to arylindane lignans

The BF3-, TsOH- or HCOOH-catalyzed dimerization of 3,4-dioxygenated cinnamate or 1-arylpropene offers a route to arylindane lignans. The structures of the products were elucidated and a mechanism is proposed for the reactions. The structures of the dimeric products assigned as aryltetralin lignans by Botta et al.

Asymmetric Lignan Synthesis: Isolariciresinol Dimethyl Ether

An asymmetric synthesis of the lignan (+)-isolariciresinol dimethyl ether 1 in nine steps and 13percent yield (83percent optical purity) from veratraldehyde is described.Veratraldehyde was converted to 6-(3,4-dimethoxybenzyl)veratraldehyde 3 by bromination, acetal formation, metalation, and coupling to 3,4-dimethoxybenzyl bromide. 3 was irradiated in the presence of SO2 to give the 3-hydroxy-1-aryl-1,3-dihydrobenzothiophene 2,2-dioxide 4, which was converted to the (R)-1-phenylethoxy derivative 5b. 5b on heating with dimethyl fumarate gave a mixture of primarily two diastereomeric cycloadducts 7b and 7b', both of which had the 1,2-trans, 2,3-trans , 3,4-cis stereochemistry.The major adduct 7b was subsequently assigned the stereochemistry 1S,2R,3S,4S.Separation and hydrogenolysis of the major adduct gave the diester 8, 1S,2R,3R, which was reduced with LiAlH4 to give (+)-isolariciresinol dimethyl ether 1.A racemic synthesis was also carried out via the methoxy sulfone 5a and its trans isomer 5a' in 33percent yield.

The Synthesis of Lignans and Related Structures using Quinodimethanes and Isobenzofurans: Approaches to the Podophyllins

Novel routes to 1-aryl-5,6-dialkoxy-1,3-dihydrobenzothiophene 2,2-dioxides (13) and to the corresponding benzofuran (8) have been developed; these species yield quinodimethanes (12) via thermal extrusion of SO2 and isobenzofurans (5c) in an acid-cat

The Preparation of Lignans via Intermolecular Cycloadditions with Quinodimethanes

Certain lignans can be prepared using, as the key step, a thermal reaction between 1-(aryl)-1,3-dihydro-5,6-dialkoxy-benzothiophen 2,2-dioxides and dienophiles.