Absolute stereochemistry of amphidinolide E

J Org Chem. 2002 Mar 8;67(5):1651-6. doi: 10.1021/jo016326n.

Abstract

The absolute configurations at eight chiral centers in amphidinolide E (1), a cytotoxic 19-membered macrolide isolated from a marine dinoflagellate Amphidinium sp., were determined to be 2R, 7R, 8R, 13S, 16S, 17R, 18R, and 19R on the basis of detailed analysis of NMR data and by chemical means.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Biological Products / chemistry*
  • Biological Products / isolation & purification*
  • Biological Products / pharmacology
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / isolation & purification*
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology
  • Catalysis
  • Dinoflagellida / chemistry*
  • Esters / chemical synthesis
  • Esters / chemistry
  • Macrolides / chemistry*
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Biological Products
  • Bridged Bicyclo Compounds, Heterocyclic
  • Esters
  • Macrolides
  • amphidinolide E