Synthesis of (-)-matairesinol, (-)-enterolactone, and (-)-enterodiol from the natural lignan hydroxymatairesinol

Org Lett. 2003 Feb 20;5(4):491-3. doi: 10.1021/ol0273598.

Abstract

[reaction: see text] We describe here a four-step semisynthetic method for the preparation of enantiomerically pure (-)-enterolactone starting from the readily available lignan hydroxymatairesinol from Norway spruce (Picea abies). Hydroxymatairesinol was first hydrogenated to matairesinol. Matairesinol was esterified to afford the matairesinyl 4,4'-bistriflate, which was deoxygenated by palladium-catalyzed reduction to 3,3'-dimethylenterolactone. Demethylation of 3,3'-dimethylenterolactone and reduction with LiAlH(4) yielded (-)-enterolactone and (-)-enterodiol, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • Furans
  • Hydrogenation
  • Lignans / chemical synthesis*
  • Lignans / chemistry
  • Picea / chemistry
  • Stereoisomerism

Substances

  • Furans
  • Lignans
  • hydroxymatairesinol
  • matairesinol
  • 2,3-bis(3'-hydroxybenzyl)butane-1,4-diol
  • 4-Butyrolactone
  • 2,3-bis(3'-hydroxybenzyl)butyrolactone