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Synthesis of pyranicin and its inhibitory action with bovine heart mitochondrial complex I.
Hattori, Yasunao; Furuhata, Shin-ichi; Okajima, Motonori; Konno, Hiroyuki; Abe, Masato; Miyoshi, Hideto; Goto, Tetsuhisa; Makabe, Hidefumi.
Org Lett ; 10(5): 717-20, 2008 Mar 06.
Article in English | MEDLINE | ID: mdl-18251547

ABSTRACT

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.


Subject(s)
Electron Transport Complex I/metabolism , Furans/chemistry , Lactones/chemistry , Mitochondria, Heart/drug effects , Acetogenins/pharmacology , Animals , Annonaceae/chemistry , Cattle , Fatty Alcohols , Furans/metabolism , Molecular Structure
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