6 research outputs found
Directed Hydrogenation of Acyclic Homoallylic Alcohols: Enantioselective Syntheses of (+)- and (−)-Laurenditerpenol
Laurenditerpenol is the first marine
natural product shown to inhibit
hypoxia-inducible factor 1 (HIF-1) activation. Preclinical studies
support that the inhibition of HIF-1 is one of the molecular targets
for antitumor drug discovery. The synthetically challenging molecular
architecture of laurenditerpenol, its absolute stereostructure, and
the biological activity of several diastereoisomers were accomplished
by our group in 2007 by diastereoselective synthesis. Herein, we report
enantioselective syntheses of both enantiomers of laurenditerpenol
involving sequential Michael addition and remote homoallylic hydroxyl
group-directed asymmetric hydrogenation at ambient temperature and
pressure as key reaction steps. The current approach is elegant and
overall more efficient than the ones previously reported in the literature