De novo synthesis of polyhydroxyl aminocyclohexanes

Org Biomol Chem. 2010 Sep 7;8(17):3908-17. doi: 10.1039/c004730a. Epub 2010 Jul 9.

Abstract

The syntheses of 12 stereochemically diverse polyhydroxyl aminocyclohexane ("aminocyclitols") derivatives are described. These short syntheses require 2-5 steps from N-(2,4-cyclohexadien-1-yl)phthalimide, which is prepared in two steps from tricarbonyl(cyclohexadienyl)iron(1+). The relative stereochemistries of the aminocyclitols were assigned by (1)H NMR spectroscopy as well as X-ray diffraction analysis.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amines / chemistry*
  • Crystallography, X-Ray
  • Cyclohexanes / chemical synthesis*
  • Hydrogenation
  • Hydroxylation
  • Models, Molecular
  • Molecular Structure

Substances

  • Amines
  • Cyclohexanes