Biomimetic asymmetric synthesis of (R)-GTRI-02 and (3S,4R)-3,4-dihydroxy-3,4-dihydronaphthalen-1(2H)-ones

Org Lett. 2012 Jul 20;14(14):3600-3. doi: 10.1021/ol301305p. Epub 2012 Jun 27.

Abstract

The NADPH-dependent tetrahydroxynaphthalene reductase (T4HNR) from Magnaporthe grisea was used for the biomimetic synthesis of (R)-GTRI-02 by stereoselective reduction of 1-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl)ethanone. This also led to the isolation of a (3S,4R)-cis-ketodiol formed by T4HNR-catalyzed reduction of the corresponding hydroxynaphthoquinone. Flaviolin and lawsone also reduced to corresponding cis-ketodiols in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Atovaquone / chemistry*
  • Biomimetics
  • Fungal Proteins / chemistry*
  • Molecular Structure
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry
  • Naphthols / chemical synthesis*
  • Naphthols / chemistry*
  • Oxidoreductases Acting on CH-CH Group Donors / chemistry*
  • Stereoisomerism
  • Tetrahydronaphthalenes / chemical synthesis*
  • Tetrahydronaphthalenes / chemistry*

Substances

  • 1-(3,6,8-trihydroxy-1-methylnaphthalen-2-yl)ethanone
  • Fungal Proteins
  • GTRI 02
  • Naphthalenes
  • Naphthols
  • Tetrahydronaphthalenes
  • tetrahydroxynaphthalene reductase
  • Oxidoreductases Acting on CH-CH Group Donors
  • Atovaquone