Collect. Czech. Chem. Commun. 1995, 60, 2165-2169

Assignment of Nitrogen Stereochemistry of Agroclavine and Elymoclavine 6-N-Oxides

Vladimír Křen, Jan Němeček and Věra Přikrylová

Institute of Microbiology, Academy of Sciences of the Czech Republic, 142 20 Prague 4, Czech Republic


Both possible 6-N-oxides of agroclavine (I) and elymoclavine (II) were prepared by hydrogen peroxide oxidation. Their 1H and 13C NMR spectra were assigned and the conformation of the D ring (half-chair) was determined. Absolute configuration at 6-N was established by NMR and molecular modelling.