70610-22-9

Upstream product

• 118799-80-7 (E)-methyl 3-<(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-1-benzofuran-5-yl>-1-propenoate 
• 125803-65-8 methyl (E)-3-<2RS,3RS)-2-(4-acetoxy-3-methoxyphenyl)-2,3-dihydro-7-methoxy-3-(methoxycarbonyl)-1-benzofuran-5-yl>-2-propenoate 
• 845883-08-1 2-(3-methoxy-4-acetyloxyphenyl)-3-methoxycarbonyl-5-(3-methoxycarbonylethyl)-7-methoxybenzo[b]furan 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 144735-56-8 5-((2-methoxycarbonyl)ethyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran 
• 144735-57-9 2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxybenzofurane 
• 144735-53-5 β-(3-methoxy-4-(benzyloxy)phenyl)-β-chloracrolein 
• 135040-87-8 Acetic acid 3-[2-(4-benzyloxy-3-methoxy-phenyl)-7-methoxy-benzofuran-5-yl]-propyl ester 
• 144735-55-7 5-(2-(methoxycarbonyl)trans-ethenyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran 
• 135040-86-7 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-(benzyloxy)phenyl)benzofuran 
• 135040-90-3 5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran-3-carbaldehyde 
• 135040-88-9 2-(4-hydroxy-3-methoxyphenyl)-5-(3-acetoxypropyl)-7-methoxybenzofuran 
• 61222-88-6 methyl 3-methoxy-4-hydroxy-5-bromocinnamate 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 

Downstream Products

• 135040-83-4 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)-3-benzo[b]furan-carbaldehyde 

Relevant academic research and scientific papers

Two new neolignan glycosides from Pittosporum glabratum Lindl.

Two new neolignan glycosides, named pittogoside A (1) and pittogoside B (2) were isolated from the roots of Pittosporum glabratum Lindl. Their structures, including the absolute stereochemistry, were determined on the basis of spectroscopic analysis and chemical evidence, with combination of circular dichroism.

Synthesis and cytotoxicity of novel benzofuran neolignan derivatives

A series of 10 related benzofuran neolignan derivatives were obtained by utilising a biomimetic reaction sequence involving oxidative dimerisation of methyl ferulate, followed by derivatisation reactions. The structures of the new compounds were confirmed by 1H NMR, elemental analysis, MS and IR. All compounds were evaluated for their cytotoxic potential against five human cancer cell lines (HL-60, SMMC-7721, A-549, SK-BR-3 and PAN-1) by the standard MTT method. The results showed that most of them exhibit potent cytotoxicity.

Antileishmanial activity, cytotoxicity and QSAR analysis of synthetic dihydrobenzofuran lignans and related benzofurans

A series of synthetic dihydrobenzofuran lignans and related benzofurans were evaluated for their cytotoxicity in a screening panel consisting of various human tumour cell lines, and for their antiprotozoal activity against L. donovani (axenic amastigotes)

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.

Synthesis of 2-substituted 3-acylbenzo[b]furans via the palladium catalysed carbonylative cyclisation of ortho-hydroxytolans

A palladium-catalysed cyclisation with concomitant carbonylation via insertion of carbon monoxide was used to prepare several potential adenosine antagonists possessing a benzo[b]furan skeleton with a formyl group in the 3-position.

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.

Regioselective Introduction of Carbon-3 Substituents to 5-Alkyl-7-methoxy-2-phenylbenzofurans: Synthesis of a Novel Adenosine A1 Receptor Ligand and Its Derivatives

By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 o