Abstract The eight possible diastereoisomeric racemates of dactyloxene-B have been synthesized by a non-stereoselective route and their configurations and predominant conformations determined by 360-MHz-1 H-NMR. and 90.5-MHz-13 C-NMR. spectroscopy. Natural dactyloxene-B and-C are shown to have the relative configuration rel-(2R, 5R, 9S, 10R) and rel-(2R, 5S, 9S, 10R), respectively.