Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) from D-xylose

J Org Chem. 2006 Feb 3;71(3):1251-3. doi: 10.1021/jo051644y.

Abstract

The first naturally occurring anhydrophytosphingosine, pachastrissamine (jaspine B), a marine compound cytotoxic toward P388, A549, HT29, and MEL28 cell lines at IC(50) = 0.01 microg/mL level, has been stereoselectively synthesized from D-xylose in 10 linear steps with 25.7% overall yield.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Sphingosine / analogs & derivatives*
  • Sphingosine / chemical synthesis
  • Sphingosine / chemistry
  • Sphingosine / toxicity
  • Stereoisomerism
  • Xylose / chemistry*

Substances

  • pachastrissamine
  • Xylose
  • Sphingosine