Enantioselective Synthesis of a Furan Lignan (+)-Sylvone

J Org Chem. 2015 Oct 16;80(20):10359-63. doi: 10.1021/acs.joc.5b01677. Epub 2015 Oct 7.

Abstract

A synthesis of natural tetrahydrofuran lignan (+)-sylvone is achieved starting from methyl allenoate in 5 steps. The synthesis begins from an enantioselective aldol reaction of methyl allenoate with 3,4-dimethoxybenzaldehyde to afford α-addition aldol adduct. Key steps for the synthesis of sylvone include an oxacyclization of the α-hydroxy allenyl adduct followed by a Michael addition of a 1,3-dithiane derivative to establish a sylvone skeleton with suitable stereoselections.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzaldehydes / chemistry
  • Catalysis
  • Furans / chemistry*
  • Heterocyclic Compounds / chemistry
  • Lignans / chemical synthesis*
  • Lignans / chemistry
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Stereoisomerism

Substances

  • Benzaldehydes
  • Furans
  • Heterocyclic Compounds
  • Lignans
  • Naphthalenes
  • tetrahydrofuran
  • 1,3-dithiane
  • allenolic acid
  • veratraldehyde