- 14-Membered resorcylic acid lactone derivatives with their anti-inflammatory from the fungus Aspergillus sp. ZJ-65
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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.
- Yin, Guo-Ping,Gong, Man,Li, Ya-Juan,Zhang, Xing,Zhu, Jing-Jing,Hu, Chang-Hua
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- Asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol and zeaenol
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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.
- Doda, Sai Reddy,Raghavendar, Avula,Haridasyam, Sharath Babu,Putta, Chandra Shekar,Rao, Bhattu Kanakadurga,Kadari, Sudhakar
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- Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones Cochliomycins A and B Using a Late-Stage Nozaki-Hiyama-Kishi Macrocyclization Reaction
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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
- Bolte, Benoit,Basutto, Jose A.,Bryan, Christopher S.,Garson, Mary J.,Banwell, Martin G.,Ward, Jas S.
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p. 460 - 470
(2015/08/11)
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- Convergent and stereoselective synthesis of (-)-zeaenol
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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.
- Kumar, Rayala Naveen,Meshram
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p. 5669 - 5677
(2015/08/03)
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- The protecting-group directed diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction: Total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues
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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
- Mohapatra, Debendra K.,Reddy, D. Sai,Mallampudi, N. Arjunreddy,Gaddam, Janardhan,Polepalli, Sowjanya,Jain, Nishant,Yadav
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p. 9683 - 9695
(2015/02/19)
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- Total syntheses of cochliomycin B and zeaenol
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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
- Gao, Yangguang,Liu, Jun,Wang, Linlin,Xiao, Ming,Du, Yuguo
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p. 2092 - 2098
(2014/04/17)
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- Asymmetric total syntheses of cochliomycin A and zeaenol
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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
- Jana, Nandan,Nanda, Samik
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p. 4313 - 4320
(2012/09/22)
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