332077-65-3

Upstream product

• 212569-07-8 2-(4-Benzyloxy-3-methoxy-phenyl)-7-hydroxy-benzofuran-5-carboxylic acid ethyl ester 
• 1486-52-8 3-methoxy-4-benzyloxybenzoyl chloride 
• 1225374-38-8 (5-formyl-2-hydroxy-3-methoxybenzyl)triphenylphosphonium chloride 
• 5438-36-8 5-iodovaniline 
• 144735-54-6 1-ethynyl-4-(benzyloxy)-3-methoxybenzene 
• 212569-04-5 2-(4-Benzyloxy-3-methoxy-phenyl)-4-bromo-furan 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 332077-64-2 2-(4-benzyloxy-3-methoxyphenyl)-5-(5,5-dimethyl-1,3-dioxan-2-yl)-7-methoxybenzofuran 

Downstream Products

• 213970-70-8 5-(2-(ethoxycarbonyl)-E-ethenyl)-7-methoxy-2-(3-methoxy-4-benzyloxyphenyl)benzofuran 
• 213970-71-9 2-(p-hydroxy-m-methoxyphenyl)-7-methoxy-5-(carbethoxy-1-propen-1-yl)benzo[b]furan 
• 156398-61-7 (E)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxyprop-1-enyl)-7-methoxybenzofuran 

Relevant academic research and scientific papers

Facile preparation of 2-arylbenzo[b]furan molecules and their anti-inflammatory effects

An efficient and practical preparation of 2-arylbenzo[b]furan molecules including natural egonol, XH-14, ailanthoidol, and unnatural derivatives is demonstrated using Sonogashira coupling, iodine induced cyclization and Wittig reaction. Anti-inflammatory effects of the prepared benzo[b]furans were examined in lipopolysaccharide (LPS)-stimulated RAW 264-7 macrophages. The results showed that ailanthoidol, XH-14 and three other unnatural derivatives (9-10, 13) inhibited significantly the production of inflammatory mediator nitric oxide without showing cytotoxicity.

An expeditious and convergent synthesis of ailanthoidol

An expeditious and concise method has been described for the synthesis of ailanthoidol through convergent route starting from vanillin. The protocol involving intramolecular Wittig as a key reaction afforded ailanthoidol in overall high yield.

A novel strategy for the synthesis of benzofuran skeleton neolignans: Application to ailanthoidol, XH-14, and obovaten

A convenient and general approach to the synthesis of the benzofuran skeleton compounds ailanthoidol, XH-14, and obovaten was developed. Starting from vanillin, a series of reactions afforded 7 in 71% yield. Treatment of 7 with n-BuLi followed by addition of substituted benzaldehydes resulted in the formation of carbinols 11 and 31. The substituted benzophenones obtained from oxidation of 11 and 31 were treated with trimethylsilyldiazomethane lithium salt to give diphenylacetylenes 15 and 33, respectively. 15 and 33 were then cyclized in the presence of either mercury acetate in acetic acid or bromine in chloroform to give 3-chloromercurio- or 3-bromobenzofuran, respectively. The 3-chloromercurio intermediates could be reduced to proton or derivatized to ester or bromide, leading to the synthesis of ailanthoidol, XH-14, and obovaten, respectively. In addition, necleophilic substitution was used to introduce a formyl or methyl group into the 3-bromobenzofuran derivatives, providing an alternative pathway to XH-14 and obovaten. The final elongation and deprotection reaction furnished the desired ailanthoidol, XH-14, and obovaten in yields of 30, 15, and 11%, respectively.

A convenient synthesis of naturally occurring benzofuran ailanthoidol

A convenient method for the synthesis of ailanthoidol starting from vanillin is provided using trimethylsilyldiazomethane lithium salt to generate a diphenylacetylene and subsequent oxymercuration cyclization of the resulting alkyne with mercury acetate in acetic acid as key steps.

A new approach to 2-aryl-7-alkoxy-benzofurans: Synthesis of ailanthoidol, a natural neolignan

A general method of synthesis of 2-aryl-7-alkoxy-benzofurans is described using a benzoannulation reaction as key step. The usefulness of this approach is shown in the new synthesis of ailanthoidol, a benzofuranoid neolignan isolated from the tree Zanthox