146173-83-3

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 5653-40-7 2-Amino-4,5-dimethoxybenzoic acid 
• 37673-11-3 2-(3,4-dimethoxyphenyl)-2-(morpholin-1-yl)acetonitrile 
• 110451-87-1 2-bromomethyl-1-iodo-4,5-dimethoxybenzene 
• 103477-58-3 2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 
• 61203-53-0 2-iodo-4,5-dimethoxybenzaldehyde 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 58432-83-0 (4,5-dimethoxy-2-iodophenyl)methyl chloride 
• 63856-82-6 1-(3,4-Dimethoxy-phenyl)-2-(2-iodo-4,5-dimethoxy-phenyl)-ethanone 
• 2859-78-1 4-Bromoveratrole 
• 55171-76-1 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one 

Downstream Products

• 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 
• 146173-85-5 (Z)-1,1-Dimethylethyl 3-amino-3-<7'-(3,4-dimethoxyphenyl)-3',4'-dimethoxybicyclo<4.2.0>octa-1',3',5'-trien-7'-yl>propenoate 
• 146173-84-4 7-(3,4-Dimethoxyphenyl)-3,4-dimethoxybicyclo<4.2.0>octa-1,3,5-triene-7-carbonitrile 

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.

Photoinduced Molecular Transformations. Part 135. New Synthesis of Taiwanin C and Justicidin E based on a Radical Cascade Process involving β-Scission of Alkoxy Radicals generated from 3- and 8-Aryl-1-ethyl-1,2-dihydrocyclobutanaphthalen-1-ols prepared by Thermolysis of (Z)-tert-...

A new general synthesis of naturally occuring phthalide lignans, based on a radical cascade process triggered by a regioselective β-scission of the alkoxy radicals generated by photolysis of the hypoiodites of 8-aryl-1-ethyl-1,2-dihydrocyclobutanaphthalen-1-ols, is described.Two phases are involved in the present synthesis of phthalide lignans; the first is a new general synthesis of tert-butyl 4-aryl-3- and 4-aryl-8-aminonaphthalene-2-carboxylates by an electrocyclic reaction of o-quinonedimethides thermally generated from (Z)-tert-butyl 3-amino-3-(bicycloocta-1,3,5-trien-7-yl)propenoates; the second is a transformation of the protected 4-aryl-3-aminonaphthalene-2-carboxylic acids into the phthalide lignans.This latter phase involves their successive conversions into 3- and 8-arylcyclobutanaphthalen-1(2H)-ones via the formation of a benzyne intermediate, and then into 3- and 8-aryl-1-ethyl-1,2-dihydrocyclobutanaphthalen-1-ols, followed by β-scission of the alkoxy radicals generated by photolysis of their hypoiodites, generated in situ with the mercury(II) oxide-iodine reagent in benzene.Simultaneous syntheses of the naturally occuring phthalide lignans taiwanin C and justicidin E were thus achieved.