61248-24-6

Upstream product

• 4718-24-5 (3aR,9S,9aR)-9-(3,4-dimethoxyphenyl)-6,7-dimethoxy-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1(3H)-one 
• 58402-11-2 (E)-diethyl 2-(3,4-dimethoxybenzylidene)succinate 
• 61223-30-1 5-IFA 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 78647-52-6 (+/-)-4-(3,4-dimethoxyphenyl)-3-methoxycarbonylbutanoic acid 
• 115061-18-2 (E)-3-(methoxycarbonyl)-4-(3,4-dimethoxyphe-nyl)but-3-enoic acid 
• 72430-92-3 4-[(3,4-dimethoxyphenyl)methyl]dihydrofuran-2-one 
• 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 
• 103477-65-2 (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 
• 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 
• 103477-58-3 2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 

Downstream Products

• 50656-79-6 (+/-)-phyltetralin 
• 521-54-0 (±)-galbulin 

Relevant academic research and scientific papers

Acid-catalyzed cyclization of 2,3-dibenzylidenesuccinates: Synthesis of lignans (±)-cagayanin and (±)-galbulin

Acid-catalyzed cyclizations of E,E-dibenzylidenesuccinate esters have been developed as an efficient synthetic route to 1-aryl-1,2-dihydronaphthalenes. This reaction has been used in the synthesis of the naturally occurring lignans (±)-cagayanin and (±)-galbulin.

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

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