59573-53-4

Upstream product

• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 103477-58-3 2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 
• 103477-60-7 1-(3,4-dimethoxyphenyl)-3-hydroxy-5,6-dimethoxy-1,3-dihydrobenzothiophene 2,2-dioxide 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 103477-67-4 6-(3,4-dimethoxybenzyl)veratrldehyde ethylene glycol acetal 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 175293-57-9 (1R,2S,3R)-1-(3,4-Dimethoxy-phenyl)-1-hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid bis-((S)-methoxycarbonyl-phenyl-methyl) ester 
• 175293-58-0 (1R,2R,3R)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid bis-((S)-methoxycarbonyl-phenyl-methyl) ester 
• 103477-64-1 (1S,3S)-1-(3,4-Dimethoxy-phenyl)-5,6-dimethoxy-3-((R)-1-phenyl-ethoxy)-1,3-dihydro-benzo[c]thiophene 2,2-dioxide 
• 624-49-7 dimethylfumarate 
• 103477-59-4 6-(3,4-dimethoxybenzyl)veratraldehyde 
• 59527-51-4 (1R,2S,3S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

The asymmetric synthesis of aryltetralin lignans: (-)-isolariciresinol dimethyl ether and (-)-deoxysikkimotoxin

The total asymmetric syntheses of (-)-isolariciresinol dimethyl ether (6) and (-)-deoxysikkimotoxin (7) have been carried out, in an attempt to exploit a synthetic strategy recently developed for the synthesis of (-)-deoxypodophyllotoxin (1, R1 = -CH2-, Ar = 3,4,5-trimethoxyphenyl). In so doing, a generalized method for the synthesis of aryltetralin lignans has been developed that should be applicable to a variety of substitution patterns and stereochemistries. A one-pot, 100% regio-selective reduction-lactonization procedure has been developed for the conversion of the ester 18b to (-)-deoxysikkimotoxin, which gave 93% isolated yield in that step.

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.