Asymmetric synthesis of (-)-tetrahydrolipstatin: an anti-aldol-based strategy

Org Lett. 2000 Aug 10;2(16):2405-7. doi: 10.1021/ol000070a.

Abstract

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.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Indicators and Reagents
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Orlistat
  • Streptomyces

Substances

  • Enzyme Inhibitors
  • Indicators and Reagents
  • Lactones
  • Orlistat