Synthesis of the aminocyclitol units of (-)-hygromycin A and methoxyhygromycin from myo-inositol

J Org Chem. 2012 Jul 6;77(13):5801-7. doi: 10.1021/jo300444b. Epub 2012 Jun 11.

Abstract

Concise and efficient syntheses of the aminocyclitol cores of hygromycin A (HMA) and methoxyhygromycin (MHM) have been achieved starting from readily available myo-inositol. Reductive cleavage of myo-inositol orthoformate to the corresponding 1,3-acetal, stereospecific introduction of the amino group via the azide, and resolution of a racemic cyclitol derivative as its diastereomeric mandelate esters are the key steps in the synthesis. Synthesis of the aminocyclitol core of hygromycin A involved chromatography in half of the total number of steps, and the aminocyclitol core of methoxyhygromycin involved only one chromatography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Cinnamates / chemical synthesis*
  • Cinnamates / chemistry
  • Cyclitols / chemistry*
  • Hygromycin B / analogs & derivatives*
  • Hygromycin B / chemical synthesis
  • Hygromycin B / chemistry
  • Inositol / analogs & derivatives
  • Inositol / chemistry*
  • Stereoisomerism

Substances

  • Cinnamates
  • Cyclitols
  • methoxyhygromycin
  • Hygromycin B
  • hygromycin A
  • Inositol