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Upstream product

• 936253-53-1 6-(4-hydroxy-3-methoxyphenyl)hexan-2-one 
• 223801-41-0 3-(4-(benzyloxy)-3-methoxyphenyl)-prop-2-enal 
• 936253-52-0 6-(3-methoxy-4-benzyloxyphenyl)hexa-3,5-dien-2-one 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 34841-06-0 3-bromo-4-methoxybenzylaldehyde 
• 121-33-5 vanillin 
• 1857-57-4 3-(3-bromo-4-methoxyphenyl)propionic acid 
• 15823-04-8 methyl 3-(4-methoxyphenyl)propionate 
• 1354834-15-3 3-(3-bromo-4-methoxyphenyl)-N-methoxy-N-methylpropanamide 
• 1354834-19-7 (E)-7-(4-(benzyloxy)-3-methoxyphenyl)-1-(3-bromo-4-methoxyphenyl)hept-6-en-3-one 
• 1354834-17-5 1-(3-bromo-4-methoxyphenyl)hept-6-en-3-one 
• 288310-70-3 3-(3-bromo-4-methoxyphenyl)-propionic acid methyl ester 

Relevant academic research and scientific papers

Enantioselective Ullmann ether couplings: Syntheses of (-)- myricatomentogenin, (-)-jugcathanin, (+)-galeon, and (+)-pterocarine

The first enantioselective Ullmann cross-coupling reactions to prepare diaryl ethers are reported. The reactions were used to prepare the diarylether heptanoid natural products (-)-myricatomentogenin, (-)-jugcathanin, (+)-galeon, and (+)-pterocarine.

Syntheses and evaluation of macrocyclic engelhardione analogs as antitubercular and antibacterial agents

The natural product engelhardione is an underexplored chemotype for developing novel treatments for bacterial infections; we therefore explored this natural product scaffold for chemical diversification and structure-activity relationship studies. Macrocy

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.

Synthesis and evaluation of macrocyclic diarylether heptanoid natural products and their analogs

The macrocyclic diarylether heptanoid (MDEH) natural products have been used in folk medicine for centuries. MDEHs are reported to exert anti-tumor properties by inhibiting the activation of NF-κB. Here we report the synthesis of a small MDEH library (first reported synthesis of racemic platycarynol) using a Grubbs cross metathesis/Ullmann cyclization strategy. Evaluation of the library led to the identification of MDEH 9b which sensitizes pancreatic cancer cells to gemcitabine mediated growth inhibition and apoptosis.

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.