66018-41-5

Usage

Uses

Used in Research Applications:
Zeaenol is used as a negative control for TAK1 inhibition studies in the field of cellular and molecular biology. It helps researchers understand the role of TAK1 in various cellular processes and the selectivity of MAP kinases.
Used in Pharmaceutical Industry:
Zeaenol is used as a potential therapeutic agent for antiviral and antiprotozoan applications due to its demonstrated activity against these pathogens. This makes it a valuable compound for the development of new drugs targeting viral and parasitic infections.
Used in Drug Development:
The active TAK1 inhibitor, (5Z)-7-Oxozeaenol, derived from Curvularia sp., is also available for use in drug development. Zeaenol can be utilized to further explore the potential of TAK1 inhibition in treating various diseases and conditions.

Upstream product

• 888723-90-8 7-methoxy-2,2-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H-benzo[d][1,3]dioxin-4-one 
• 1605301-78-7 5-{(E)-3-[(4S,5S)-5-{(S)-1-[(tert-butyldimethylsilyl)oxy]allyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-1-en-1-yl}-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 1605301-79-8 (S)-pent-4-en-2-yl 2-{(E)-3-[(4S,5S)-5-{(S)-1-[(tert-butyldimethylsilyl)oxy]allyl}-2,2-dimethyl-1,3-dioxolan-4-yl]prop-1-en-1-yl}-6-hydroxy-4-methoxybenzoate 
• 1605301-80-1 (S)-pent-4-en-2-yl 2-hydroxy-6-[(E)-3-{(4S,5R)-5-[(S)-1-hydroxyallyl]-2,2-dimethyl-1,3-dioxolan-4-yl}prop-1-en-1-yl]-4-methoxybenzoate 
• 1278520-08-3 cochliomycin B 
• 1605301-81-2 (3aS,4S,5E,8S,15E,17aS)-4-(tert-butyldimethylsilyloxy)-11-hydroxy-13-methoxy-2,2,8-trimethyl-7,8,17,17a-tetrahydro-3aH-benzo[c][1,3]dioxolo[4,5-h][1]oxacyclotetradecin-10(4H)-one 
• 3673-14-1 2,3:4,5-di-D-isopropylidene-D-xylose diethyl dithioacetal 
• 1628535-46-5 (4S,5R,6R,10S,E)-4,5-bis(benzyloxy)-10-((tert-butyldimethylsilyl)oxy)undeca-1,7-dien-6-ol 
• 99096-90-9 (2R,3S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol 
• 150406-35-2 (S)-tert-butyldimethyl(pent-4-yn-2-yloxy)silane 
• 116444-16-7 (2R,3S)-2,3-bis(benzyloxy)hex-5-en-1-ol 

Relevant academic research and scientific papers

14-Membered resorcylic acid lactone derivatives with their anti-inflammatory from the fungus Aspergillus sp. ZJ-65

Two new 14-membered resorcylic acid lactone derivatives, ascarpins A (1) and B (2), together with three related known compounds (3–5) were isolated from the fungus Aspergillus sp. ZJ-65, obtaining from the intestine of grass carp. These structures were elucidated on the basis of extensive spectroscopic methods, chemical conversion, and comparison with literature. All isolates were tested for their inhibitory activity against LPS-induced NO production in RAW 264.7 macrophages. Among them, compounds 1–4 exhibited potential anti-inflammatory activity with IC50 values ranging from 7.6 to 48.3 μM.

Asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol and zeaenol

An efficient, short and, a convenient asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol (2) and zeaenol (1) have been achieved in 7 and 9 linear steps with the high overall yield of 32% and 21% respectively, from the known intermediate 13. Mitsunobu inversion, De Brabander's protocol for macrolactonisation, Heck cross-coupling, diastereoselective alkyne aldehyde coupling and Ohira-Bestmann alkynylation are the key reactions.

Convergent and stereoselective synthesis of (-)-zeaenol

Stereoselective synthesis of (-)-zeaenol has been accomplished from d-xylose as a chiral pool starting material. The key steps of this convergent synthetic strategy involves a Stille coupling, a Noyori reduction, a Julia-Kocienski olefination and a macrolactonization to obtain (-)-zeaenol. We have also explored a Sonogashira coupling along with a Trost protocol for the intramolecular hydrosilylation on the homopropargylic alcohol system as an alternative synthetic approach to this molecule.

Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones Cochliomycins A and B Using a Late-Stage Nozaki-Hiyama-Kishi Macrocyclization Reaction

The natural products cochliomycin A (1) and cochliomycin B (2), two resorcylic acid lactones obtained from marine sources, have been prepared in a concise and stereocontrolled manner from the readily accessible building blocks 4-6. Olefin cross-metathesis

The protecting-group directed diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction: Total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues

The stereoselective total synthesis of zeaenol and 7-epi-zeaenol is achieved in a convergent manner using Julia-Kocienski olefination, protecting group-directed intermolecular diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction, De Brabander's lactoniza

Total syntheses of cochliomycin B and zeaenol

Divergent syntheses of two 14-membered resorcylic acid lactones (RALs), cochliomycin B (6) and zeaenol (22), have been accomplished. The key feature in our strategy was the facile construction of three contiguous stereogenic centers in the title molecules

Asymmetric total syntheses of cochliomycin A and zeaenol

The first asymmetric total syntheses of two resorcylic acid lactones (RALs) - cochliomycin A and zeaenol - have been achieved in a divergent way. The main highlight of our strategy involves successful application of stereoselecive Keck allylation and Julia-Kocienski olefination to access an advanced intermediate, by starting from L-tartaric acid as a chiral pool compound. This intermediate is coupled with a trisubstituted benzoic acid to afford a common RCM precursor for both target molecules. Ring-closing metathesis at a late stage, followed by functional group manipulation, yielded the target molecules in an efficient way. Two resorcylic acid lactones (RALs) - cochliomycin A and zeaenol - have been synthesized for the first time by an enantiodivergent route from the common chiral pool compound L-tartaric acid. Copyright