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 acetogenins such as cis-solamin.
Hattori
Yasunao
Y
Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minaniminowa Kami-ina, Nagano 399-4598, Japan.
Furuhata
Shin-ichi
S
Okajima
Motonori
M
Konno
Hiroyuki
H
Abe
Masato
M
Miyoshi
Hideto
H
Goto
Tetsuhisa
T
Makabe
Hidefumi
H
D054378:Acetogenins / Q000494:pharmacology; D000818:Animals; D029061:Annonaceae / Q000737:chemistry; D002417:Cattle; D042967:Electron Transport Complex I / Q000378:metabolism*; D005233:Fatty Alcohols; D005663:Furans / Q000737:chemistry* / Q000378:metabolism; D007783:Lactones / Q000737:chemistry*; D008929:Mitochondria, Heart / Q000187:drug effects*; D015394:Molecular Structure
D054378:Acetogenins; D005233:Fatty Alcohols; D005663:Furans; D007783:Lactones; C519987:cis-solamin; C475590:pyranicin; D042967:Electron Transport Complex I