213970-70-8

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 213970-73-1 (E)-3-[3-(4-Benzyloxy-3-methoxy-phenylethynyl)-4-hydroxy-5-methoxy-phenyl]-acrylic acid ethyl ester 
• 213970-69-5 trans-ethyl 3-(5-bromo-4-hydroxy-3-methoxyphenyl)propenoate 
• 144735-54-6 1-ethynyl-4-(benzyloxy)-3-methoxybenzene 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 332077-65-3 2-(4-benzyloxy-3-methoxyphenyl)-7-methoxybenzo[b]furan-5-carboxaldehyde 
• 82101-76-6 ethyl (E)-3-(tributylstannyl)acrylate 
• 515814-05-8 2-[4-(benzyloxy)-3-methoxyphenyl]-5-bromo-7-methoxybenzofuran 
• 56897-51-9 5-bromo-7-methoxy-2-nitrobenzofuran 
• 5034-74-2 5-bromo-3-methoxysalicylaldehyde 
• 515814-03-6 5-bromo-7-methoxy-2-bromobenzofuran 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 212569-04-5 2-(4-Benzyloxy-3-methoxy-phenyl)-4-bromo-furan 

Downstream Products

• 144735-57-9 2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxybenzofurane 
• 156398-61-7 (E)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxyprop-1-enyl)-7-methoxybenzofuran 
• 213970-71-9 2-(p-hydroxy-m-methoxyphenyl)-7-methoxy-5-(carbethoxy-1-propen-1-yl)benzo[b]furan 

Relevant academic research and scientific papers

An alternate method for the synthesis of 2-aryl/alkyl-5-bromo-7-methoxy benzofurans; application to the synthesis of Egonol, Homoegonol, and analogs via Heck reaction

We herein report the general, versatile, and convenient method for the synthesis of 2-arly/alkyl-5-bromo-7-methoxy benzofurans from easily available o-Vanillin in five steps. These benzofurans was successfully converted into biological active natural products Egonol, Homoegonol, and analogous on applying Heck reaction using ethyl/methyl acrylate in the presence of palladium catalyst.

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.

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.

Total synthesis of ailanthoidol and precursor XH14 by stille coupling

Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the

Synthesis of natural products possessing a benzo[b]furan skeleton

A related synthetic strategy has been used to prepare two natural products XH-14 and ailanthoidol) which possess a benzo[b]furan skeleton. The synthesis of XH-14 involved the use of a palladium-catalyzed cyclization with concomitant carbonylation via insertion of carbon monoxide to introduce regioselectively a formyl group in the 3-position.

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