Synthetic studies on the solanacol ABC ring system by cation-initiated cascade cyclization: implications for strigolactone biosynthesis

Org Biomol Chem. 2011 Aug 7;9(15):5350-3. doi: 10.1039/c1ob05751k. Epub 2011 Jun 24.

Abstract

We report a new method for constructing the ABC ring system of strigolactones, in a single step from a simple linear precursor by acid-catalyzed double cyclization. The reaction proceeds with a high degree of stereochemical control, which can be qualitatively rationalized using DFT calculations. Our concise synthetic approach offers a new model for thinking about the (as yet) unknown chemistry that is employed in the biosynthetic pathways leading to this class of plant hormones.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Cations / chemistry
  • Cyclization
  • Lactones / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Plant Growth Regulators / chemical synthesis
  • Plant Growth Regulators / chemistry
  • Quantum Theory*
  • Stereoisomerism

Substances

  • (4-hydroxy-5,8-dimethyl-3-(4-methyl-5-oxo-2,5-dihydrofuran-2-yloxy)methylene)-3a,4-dihydro-3H-indeno(1,2-b)furan-2(8bH)-one
  • Cations
  • Lactones
  • Plant Growth Regulators
  • strigol