Asymmetric synthesis of (-)-tetrahydrolipstatin: an anti-aldol-based strategy.
A stereoselective synthesis of (-)-tetrahydrolipstatin is described. The synthesis involves an asymmetric ester derived titanium enolate anti-aldol reaction, a nitro-aldol reaction to append the C-2' C(11) side chain, and a diastereoselective reduction of a beta-hydroxy ketone to an anti-1,3-diol functionality followed by its elaboration to (-)-tetrahydrolipstatin.
Ghosh
A K
AK
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA. arunghos.uic.edu
Fidanze
S
S
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D000077403:Orlistat; D013302:Streptomyces
D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D007783:Lactones; D000077403:Orlistat