Racemic total synthesis of dactyloidin and demethyldactyloidin through the DL-proline-catalyzed Knoevenagel condensation/[4 + 2] cycloaddition cascade

Org Biomol Chem. 2015 Oct 21;13(39):9977-83. doi: 10.1039/c5ob01636c.

Abstract

An efficient approach towards the first racemic total synthesis of dactyloidin (2) and demethyldactyloidin (3) is described. Their oxygen-bridged tricyclic ketal systems were rapidly constructed by using a remarkable biomimetic Knoevenagel condensation/[4 + 2] cycloaddition cascade as the critical strategy and the 1,5-dicarbonyl segment was assembled by Grignard addition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cycloaddition Reaction / methods*
  • Heterocyclic Compounds, Bridged-Ring / chemical synthesis*
  • Heterocyclic Compounds, Bridged-Ring / chemistry
  • Methylation
  • Myristicaceae / chemistry*
  • Proline / chemistry*
  • Stereoisomerism

Substances

  • Heterocyclic Compounds, Bridged-Ring
  • dactyloidin
  • Proline