Synthesis of Pyranicin and Its Inhibitory Action with Bovine Heart Mitochondrial Complex I

Total synthesis of pyranicin was achieved using Cl2Pd(CH3CN)2-catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of this compound for mitochondrial NADH−ubiquinone oxidoreductase (complex I) was slightly poorer than that of ordinary mono-THF acetog...

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Bibliographic Details
Published in:Organic letters 2008-03, Vol.10 (5), p.717-720
Main Authors: Hattori, Yasunao, Furuhata, Shin-ichi, Okajima, Motonori, Konno, Hiroyuki, Abe, Masato, Miyoshi, Hideto, Goto, Tetsuhisa, Makabe, Hidefumi
Format: Article
Language:English
Subjects:
Acetogenins - pharmacology
Animals
Annonaceae - chemistry
Cattle
Electron Transport Complex I - metabolism
Fatty Alcohols
Furans - chemistry
Furans - metabolism
Lactones - chemistry
Mitochondria, Heart - drug effects
Molecular Structure
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Summary:Total synthesis of pyranicin was achieved using Cl2Pd(CH3CN)2-catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of this compound for mitochondrial NADH−ubiquinone oxidoreductase (complex I) was slightly poorer than that of ordinary mono-THF acetogenins such as cis-solamin.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702902w