Synthesis of key fragments of leiodelide A

Org Lett. 2011 Jun 17;13(12):3246-9. doi: 10.1021/ol201183f. Epub 2011 May 25.

Abstract

The synthesis of all key fragments of the marine macrolide leiodelide A is described. The polyoxygenated northern subunit is derived from d-xylose, while the southern subunit is rapidly assembled via an aldol reaction and Horner-Wadsworth-Emmons olefination. This highly convergent approach will allow for rapid modification and assembly of several isomers of leiodelide A, which may be necessary considering the assignment of leiodelide B has been previously shown to be incorrect.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Drug Screening Assays, Antitumor
  • Female
  • HL-60 Cells
  • Humans
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Macrolides / pharmacology
  • Molecular Structure
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry
  • Oxazoles / pharmacology
  • Stereoisomerism
  • Xylose / chemistry

Substances

  • Antineoplastic Agents
  • Macrolides
  • Oxazoles
  • leiodelide A
  • leiodelide B
  • Xylose