Efficient synthetic approach to potent antiproliferative agent hippuristanol via Hg(II)-catalyzed spiroketalization.
The steroidal natural product hippuristanol targets eukaryotic translation initiation factor (eIF)4A which plays a pivotal role in translation in eukaryotic cells. Now an efficient synthesis of hippuristanol from 11-ketotigogenin is reported. The synthesis features a rapid construction of a spiroketal unit via Hg(OTf)(2)-catalyzed oxidation/spiroketalization of the 3-alkyn-1,7-diol motif.
Ravindar
Kontham
K
Département de Chimie, Université de Sherbrooke, Sherbrooke, QC, J1K 2R1, Canada.
Reddy
Maddi Sridhar
MS
Lindqvist
Lisa
L
Pelletier
Jerry
J
Deslongchamps
Pierre
P
D002384:Catalysis; D049109:Cell Proliferation / Q000187:drug effects*; D005663:Furans / Q000737:chemistry*; D008628:Mercury / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry*; D013261:Sterols / Q000138:chemical synthesis* / Q000494:pharmacology
D005663:Furans; D013141:Spiro Compounds; D013261:Sterols; C510125:hippuristanol; C520774:spiroketal; D008628:Mercury