Synthetic approach to hypoxyxylerone, novel inhibitor of topoisomerase I.
[reaction: see text] A potential route to the topoisomerase I inhibitor hypoxyxylerone is demonstrated by a highly convergent synthesis of the penta(O-methyl) derivative. The key step in the approach is an anionic homo-Fries rearrangement, little used to date in natural product synthesis and employed here for the first time with a dinaphthalenic substrate, to access the pentacyclic system of hypoxyxylerone.
Piettre
Arnaud
A
Université Joseph Fourier de Grenoble, Chimie Recherche (LEDSS), 38041 Grenoble Cedex, France.
Chevenier
Emmanuel
E
Massardier
Christine
C
Gimbert
Yves
Y
Greene
Andrew E
AE
D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000494:pharmacology; D009183:Mycotoxins / Q000138:chemical synthesis; D059004:Topoisomerase I Inhibitors; D014966:Xanthenes / Q000138:chemical synthesis
D004791:Enzyme Inhibitors; D006576:Heterocyclic Compounds, 4 or More Rings; D009183:Mycotoxins; D059004:Topoisomerase I Inhibitors; D014966:Xanthenes; C011759:dibenzoxanthenes; C471504:hypoxyxylerone