1422971-02-5

Upstream product

• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 33279-69-5 2,2-dimethyl-7-hydroxy-2H-1-benzopyran-6-carboxaldehyde 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 115-18-4 2-methyl-3-buten-2-ol 
• 21422-02-6 2,4-dihydroxy-5-(3’-methyl-2’-buten-1’-yl)benzaldehyde 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 108-46-3 recorcinol 
• 31005-72-8 2,2-dimethylchroman-7-ol 
• 32268-32-9 7-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-carbaldehyde 
• 269409-70-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 

Relevant academic research and scientific papers

A protecting group-free divergent synthesis of natural benzofurans via one-pot synthesis of 2-bromo-6-hydroxybenzofurans

2-Bromo-6-hydroxybenzofurans are potentially versatile intermediates for the divergent synthesis of numerous benzofuran-based natural products and their analogues. Herein we report the first one-pot strategy for the efficient synthesis of 2-bromo-6-hydrox

Functional group manoeuvring for tuning stability and reactivity: Synthesis of cicerfuran, moracins (D, E, M) and chromene-fused benzofuran-based natural products

The protecting group manoeuvring as a strategy was applied for tuning the stability and reactivity of 4-(2,2-dibromovinyl)benzene-1,3-diol (12a) and 6-(2,2-dibromovinyl)-2,2-dimethylchroman-7-ol (22) in the domino synthesis of benzofuran-based natural products (1-8). The functional group demands and their impact on the reactivity driven by electronic effects were successfully managed by varying the protecting groups with substituted gem-dibromovinylphenols in domino couplings and triarylbismuth reagents under palladium-catalyzed conditions. This approach paved the way for the synthesis of moracin M (1) and cicerfuran (2), and the first time synthesis of moracin D (3) and moracin E (4) along with chromene-fused benzofuran-based natural products (5-8) in overall good yields.

Synthetic methods for Gramniphenols F and G, Cicerfuran, Morunigrol C and its Derivative

The present invention relates to a method for preparing natural benzofurans including gramniphenol F, gramniphenol G, morunigrol C and 3andprime;,5andprime;-di-O-methyl analogues thereof and cicerfuran by using 2,4-dihydroxybenzaldehyde, 5-bromoresorcinol and sesamol. In the method according to the present invention, region-selective prenylation, Ramirez gem-dibromo olefination, Miyaura borylation and Suzuki coupling are used. In addition, the compounds were determined for anti-inflammatory effects through a test for production of nitrogen oxide in liposaccharide-induced RAW-264.7 macrophages. All of the compounds show weak to medium (16-42%) inhibitory activities, are not toxic and have an IC_50 value of 9.1 to 25.2 andmu;M.COPYRIGHT KIPO 2017

Unified syntheses of gramniphenols F and G, cicerfuran, morunigrol C and its derivative

The first syntheses of natural benzofurans, gramniphenols F and G, morunigrol C and its 3′,5′-di-O-methyl analogue along with the synthesis of cicerfuran are achieved by a unified synthetic sequence using 7-hydroxycoumarin, 5-bromoresorcinol, 2,4-dihydroxybenzaldehyde, and sesamol as building blocks. Ramirez gem-dibromoolefination, Miyaura borylation, Suzuki coupling have been successfully exploited in the synthesis. Additionally, their anti-inflammatory effects were also investigated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages. The compounds exhibited significant inhibition of iNOS mediated nitric oxide (NO) production with no cytotoxicity at 10 μM concentration and IC50 values are found in the range from 9.1 to 25.2 μM.