Stereoselective synthesis of L-threo-sphingosine, L-threo-sphinganine, D-threo-sphingosine, and D-threo-sphinganine via oxazoline formation and olefin cross-metathesis; potent protein kinase C inhibitor analogues

Arch Pharm Res. 2007 Feb;30(2):167-71. doi: 10.1007/BF02977690.

Abstract

In this study, we explored a convenient and concise route for synthesis of L-threo-sphingosine, D-threo-sphingosine, L-threo-sphinganine and D-threo-sphinganine from commercially available L- or D-serine. The key steps are the simple preparation of trans-oxazoline and intermolecular olefin cross metathesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Molecular Structure
  • Oxazoles / chemistry*
  • Protein Kinase C / antagonists & inhibitors*
  • Protein Kinase Inhibitors* / chemical synthesis
  • Protein Kinase Inhibitors* / chemistry
  • Protein Kinase Inhibitors* / pharmacology
  • Sphingosine / analogs & derivatives*
  • Sphingosine / chemical synthesis
  • Sphingosine / chemistry
  • Sphingosine / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Alkenes
  • Oxazoles
  • Protein Kinase Inhibitors
  • Protein Kinase C
  • Sphingosine
  • safingol