De novo synthesis of polyhydroxyl aminocyclohexanes

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 ¹H NMR spectroscopy as well as X-ray diffraction analysis.