De novo synthesis of polyhydroxyl aminocyclohexanes.
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.
Sar
Anobick
A
Department of Chemistry, Marquette University, P. O. Box 1881, Milwaukee, WI, USA.
Lindeman
Sergey
S
Donaldson
William A
WA
D000588:Amines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003510:Cyclohexanes / Q000138:chemical synthesis*; D006865:Hydrogenation; D006900:Hydroxylation; D008958:Models, Molecular; D015394:Molecular Structure
D000588:Amines; D003510:Cyclohexanes