Synthesis of pyranicin and its deoxygenated analogues and their inhibitory action with bovine heart mitochondrial complex I

Total synthesis of pyranicin and its deoxygenated analogues was achieved using Cl 2Pd(CH 3CN) 2 catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of these compounds for mitochondrial NADH–ubiquinone oxidoreductase (complex I) was poorer than those...

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Bibliographic Details
Published in:Tetrahedron 2008-08, Vol.64 (33), p.7695-7703
Main Authors: Furuhata, Shin-ichi, Hattori, Yasunao, Okajima, Motonori, Konno, Hiroyuki, Abe, Masato, Miyoshi, Hideto, Goto, Tetsuhisa, Makabe, Hidefumi
Format: Article
Language:English
Subjects:
Annonaceous acetogenin
Antitumor
Mitochondrial complex I
Stereoselective synthesis
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Summary:Total synthesis of pyranicin and its deoxygenated analogues was achieved using Cl 2Pd(CH 3CN) 2 catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of these compounds for mitochondrial NADH–ubiquinone oxidoreductase (complex I) was poorer than those of ordinary mono-THF acetogenins such as annonacin. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.06.028