Ivorenolide B, an immunosuppressive 17-membered macrolide from Khaya ivorensis: structural determination and total synthesis

Org Lett. 2014 Apr 4;16(7):2062-5. doi: 10.1021/ol500667d. Epub 2014 Mar 25.

Abstract

Ivorenolide B (1), an unprecedented 17-membered macrolide featuring conjugated acetylenic bonds and four chiral centers, was isolated from Khaya ivorensis. The structure of 1 was fully determined by spectroscopic analysis and total syntheses of its four most possible stereoisomers. Compound 1 showed significant immunosuppressive activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / isolation & purification*
  • Immunosuppressive Agents / pharmacology*
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology*
  • Meliaceae / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism

Substances

  • Immunosuppressive Agents
  • Macrolides
  • ivorenolide B