Synthesis and structural revision of symbiodinolide C23-C34 fragment

J Org Chem. 2009 Jul 3;74(13):4797-803. doi: 10.1021/jo900546k.

Abstract

Stereoselective synthesis of the C23-C34 fragment of symbiodinolide, which possesses the originally proposed stereochemistry, and its diastereomers was achieved in 19 steps from L-aspartic acid, respectively. Comparison of spectroscopic data of the synthetic products with those of the degraded product of symbiodinolide led to a structural revision of the C23-C34 fragment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspartic Acid / chemistry*
  • Catalysis
  • Macrocyclic Compounds / chemical synthesis*
  • Macrocyclic Compounds / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism

Substances

  • Macrocyclic Compounds
  • symbiodinolide
  • Aspartic Acid