76678-64-3

Upstream product

• 621-59-0 isovanillin 
• 100-39-0 benzyl bromide 
• 75-07-0 acetaldehyde 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 108-05-4 vinyl acetate 
• 100-44-7 benzyl chloride 
• 121174-59-2 C₁₈H₁₈O₄ 

Downstream Products

• 1330753-35-9 1-(3-bromo-4-methoxyphenyl)-7-(3-hydroxy-4-methoxyphenyl)heptan-3-one 
• 1021172-47-3 1-(4-bromophenyl)-7-(3-hydroxy-4-methoxyphenyl)heptan-3-one 
• 1354834-22-2 1-(3-bromo-4-(methoxymethoxy)phenyl)-7-(3-hydroxy-4-methoxyphenyl)heptan-3-one 
• 1391150-62-1 (E)-1-(4-bromophenyl)-7-(3-hydroxy-4-methoxyphenyl)hept-1-en-3-one 
• 1391150-63-2 (E)-1-(2-bromophenyl)-7-(3-hydroxy-4-methoxyphenyl)hept-1-en-3-one 
• 1391150-49-4 1-(2-bromophenyl)-7-(3-hydroxy-4-methoxyphenyl)heptan-3-one 
• 1330753-34-8 (E)-1-(3-bromo-4-methoxyphenyl)-7-(3-hydroxy-4-methoxyphenyl)hept-1-en-3-one 

Relevant academic research and scientific papers

Synthesis and antibacterial evaluation of macrocyclic diarylheptanoid derivatives

Bacterial infections, caused by Mycobacterium tuberculosis and other problematic bacterial pathogens, continue to pose a significant threat to global public health. As such, new chemotype antibacterial agents are desperately needed to fuel and strengthen the antibacterial drug discovery and development pipeline. As part of our antibacterial research program to develop natural product-inspired new antibacterial agents, here we report synthesis, antibacterial evaluation, and structure–activity relationship studies of an extended chemical library of macrocyclic diarylheptanoids with diverse amine, amide, urea, and sulfonamide functionalities. Results of this study have produced macrocyclic geranylamine and 4-fluorophenethylamine substituted derivatives, exhibiting moderate to good activity against M. tuberculosis and selected Gram-positive bacterial pathogens.

PROCESS FOR THE PREPARATION OF ADVANTAME

A novelprocess for the preparation of N—[N-[3-(3-hydroxy-4-methoxyphenyl)-propyl]-L-α-aspartyl]-L-phenylalanine-1-methyl ester is described. It comprises, reacting isovanillin or its derivative with vinyl acetate followed by reductive condensation with L-[α-aspartyl]-L-phenylalanine-1-methyl ester.

Microwave-assisted synthesis of macrocycles via intramolecular and/or bimolecular Ullmann coupling

Microwave-assisted synthesis of macrocyclic diaryl ethers via intramolecular and/or bimolecular Ullmann coupling is described. Using the optimized conditions, a panel of macrocycles, with different substitution patterns, ring sizes, and linkers, has been successfully synthesized using microwave irradiation. To the best of our knowledge, this work represents the first examples of the microwave-assisted synthesis of macrocyclic diaryl ethers via intramolecular and/or bimolecular Ullmann coupling.

Total synthesis and structural revision of engelhardione

The total synthesis of the macrocyclic natural product engelhardione is reported. This effort led to the structural revision of the published structure of engelhardione to that of pterocarine. The revision reflects the change of the substitution pattern of one phenyl ether ring from the meta to the para position. To confirm, pterocarine (2) and its close regioisomer 3 were subsequently synthesized for comparison. Moreover, to the best of our knowledge, our synthesis of 1 represents the first example of a 14-membered macrocyclic diarylheptanoid with a meta-meta substitution pattern at the diphenyl ether moiety.