The microtubule‐stabilizing agent 1 was obtained through extensive modification (colored circles) of the structure of natural epothilone. Despite these structural differences, the biological potency of 1 is comparable with that of epothilone A and taxol!
trans‐1‐(2‐Pyridyl)‐, trans‐1‐(3‐pyridyl)‐, trans‐1(2‐furyl)‐, and trans‐1(3‐furyl)‐2‐phenyl epoxides with enantiomeric purities ranging from 96.8 to 99.8% [in favor of the (+, EtOH)‐isomer] are obtained in two steps from pure (R,R,R)‐oxathiane which is recovered (85‐90%) and reused. The chiral bidentate ligand 2‐phenyl‐(S) ‐1‐(2‐pyridyl)ethanol with 99.6% ee was obtained in three steps and 67% overall isolated yield.
Ein Mikrotubulistabilisator (1) wurde durch starke Modifizierung (Kreise im Bild) der natürlichen Epothilon‐Grundstruktur erhalten. Trotz deutlich unterschiedlicher Struktur ist die biologische Aktivität von 1 vergleichbar mit der von Epothilon A oder Taxol! Die Entdeckung von 1 zeigt, wie die starke Modifizierung von Naturstoffen zu neuen strukturellen Templaten für die Hemmung von Mikrotubuli und damit vielleicht zu neuen Wirkstoffen führen kann.
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