Systematic strategy for the synthesis of cyanobacterin and its stereoisomers. 2. Asymmetric total synthesis of the 2- and 3-epimers of dechloro-cyanobacterin

Biosci Biotechnol Biochem. 2003 Oct;67(10):2215-23. doi: 10.1271/bbb.67.2215.

Abstract

Stereocontrolled total syntheses of the (2S,3R)- and (2R,3S)-isomers of the non-chlorinated analog of cyanobacterin, a potent photosynthesis inhibitor, were achieved. Since both the (2R,3R)- and (2S,3S)-isomers of this compound had been previously synthesized from the same starting material, a systematic strategy for the synthesis of all stereoisomers could be established.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis*
  • Alkynes / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkynes
  • dechloro-cyanobacterin
  • cyanobacterin
  • 4-Butyrolactone