Enantioselective total synthesis of eurylene, 14-deacetyl eurylene, and their 11-epimers: the relation between ionophoric nature and cytotoxicity.
[structure: see text] Enantioselective synthesis of eurylene, 14-deacetyl eurylene, and their 11-epimers was achieved. The characteristic structural feature of these compounds is two tetrahydrofuran (THF) rings substituted in different stereochemistry. The synthetic approach involves nonstereoselective THF ring formation to afford both segments from a common precursor. We also investigated their ionophoric nature and cytotoxicity. The complexation of these compounds with K(+) might be related to their cytotoxic activity.
Hioki
Hideaki
H
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
Yoshio
Suzuyo
S
Motosue
Masatoshi
M
Oshita
Yuka
Y
Nakamura
Yukari
Y
Mishima
Daisaku
D
Fukuyama
Yoshiyasu
Y
Kodama
Mitsuaki
M
Ueda
Keisuke
K
Katsu
Takashi
T
D035701:Eurycoma; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D006801:Humans; D007476:Ionophores / Q000737:chemistry*; D007624:KB Cells; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D011188:Potassium / Q000737:chemistry; D014315:Triterpenes / Q000138:chemical synthesis*
C493364:14-deacetyl eurylene; D005663:Furans; D007476:Ionophores; D014315:Triterpenes; C493363:eurylene; C018674:tetrahydrofuran; D011188:Potassium