3687-28-3

Upstream product

• 50816-75-6 5-phenyl-1,2,3-trimethoxybenzene 
• 70654-71-6 4-bromo-2,6-dimethoxyphenol 
• 98-80-6 phenylboronic acid 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 634-36-6 1,2,3-trimethoxybenzene 
• 125106-77-6 2-(benzyloxy)-5-bromo-1,3-dimethoxybenzene 
• 5150-42-5 2,3-dimethoxyphenol 
• 57197-26-9 5,6,6-trimethoxycyclohexa-2,4-dien-1-one 
• 7028-41-3 5-phenylresorcinol 
• 493-72-1 5-phenyl-cyclohexane-1,3-dione 
• 64326-17-6 3,5-dimethoxybiphenyl 

Downstream Products

• 6249-27-0 3,4,5-Trihydroxy-biphenyl 

Relevant academic research and scientific papers

Palladium-catalyzed regioselective synthesis of oxygenated biphenyls

Palladium-catalyst-mediated Michael addition reaction of arylboronic acids to cyclohexa-2,4-dienones followed by aromatization sequence in one-pot furnished several oxygenated biphenyl derivatives. Application of the developed methodology was successfully

First Enantioselective Synthesis of Surinamensinol B and a Non-Natural Polysphorin Analogue by a Two-Stereocentered Hydrolytic Kinetic Resolution

An efficient and economical approach to the synthesis of antitumor and anti-inflammatory surinamensinol B (1) and antimalarial polysphorin analogue 2 has been achieved with high enantiomeric purity (96 % ee) by starting from commercially available 3,4,5-trimethoxybenzaldehyde. The key steps of the strategy include a Co-catalyzed two-stereocentered hydrolytic kinetic resolution (HKR) of racemic 2-[(methoxymethoxy)(3,4,5-trimethoxyphenyl)methyl]oxirane (13) as the chiral inducing step followed by a Mitsunobu reaction. Chiral epoxide 14 and chiral diol 15 were utilized in the syntheses of both compounds.

Suzuki-Miyaura coupling of halophenols and phenol boronic acids: Systematic investigation of positional isomer effects and conclusions for the synthesis of phytoalexins from pyrinae

The Suzuki-Miyaura couplings of o-, m-, and p-halophenols with o-, m-, and p-phenol boronic acids were investigated for all combinations under standardized conditions, using Pd/C as a heterogeneous catalyst and water as a solvent. In the case of iodophenols, conventional heating was used, while for bromophenols significantly better results could be obtained using microwave irradiation. This systematic study revealed that 2,4′-biphenol is particularly difficult to access, irrespective of the starting materials used, but that these difficulties can be overcome by using different additives. The conclusions drawn from this investigation allowed us to identify conditions for the protecting group-free or minimized total synthesis of biaryl-type phytoalexins. These compounds possess antibacterial activity and are produced by fruit trees as a response to microbial infection.

Biosynthesis of the biphenyl phytoalexin aucuparin in Sorbus aucuparia cell cultures treated with Venturia inaequalis

Aucuparin is the most widely distributed biphenyl phytoalexin in the rosaceous subtribe Pyrinae, which includes the economically important fruit trees apple and pear. The biphenyl scaffold is formed by biphenyl synthase, which catalyzes biosynthesis of 3,5-dihydroxybiphenyl. Conversion of this precursor to aucuparin (3,5-dimethoxy-4-hydroxybiphenyl) was studied in cell cultures of Sorbus aucuparia after treatment with an elicitor preparation from the scab-causing fungus Venturia inaequalis. The sequence of the biosynthetic steps detected was O-methylation - 4-hydroxylation - O-methylation. The two alkylation reactions were catalyzed by distinct methyltransferases, which differed in pH and temperature optima as well as stability. Biphenyl 4-hydroxylase was a microsomal cytochrome P450 monooxygenase, whose activity was appreciably decreased by the addition of established P450 inhibitors. When fed to V. inaequalis-treated S. aucuparia cell cultures, radioactively labeled 3,5-dihydroxybiphenyl was not only incorporated into aucuparin but also into the dibenzofuran eriobofuran, the accumulation of which paralleled that of aucuparin. However, biphenyl 2′-hydroxylase activity proposed to be involved in dibenzofuran formation was detected in neither microsomes nor cell-free extracts in the presence of NADPH and 2-oxoglutarate, respectively. Nevertheless, a basis for studying biphenyl biosynthesis at the gene level is provided.