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Stereochemistry of the roridins. Diastereomers of roridin E
1Department of Chemistry and Biochemistry, and Joint Institute for Food Safety and Nutrition, University of Maryland, College Park, Maryland 20742, USA. bj6@umail.umd.edu
Abstract:
A careful investigation of cultures of Myrothecium verrucaria has shown that this fungus produces all four roridin E isomers (3a-d), diastereomeric at the C-6' and C-13' centers. The stereochemistries at these centers were established by a combination of X-ray crystallographic analysis, NMR spectroscopy, and chemical transformations. NMR data from these and other macrocyclic trichothecenes allows for the assignment of configurations at the C-6' and C-13' centers for most of these compounds, the exceptions being those congeners having a C-4' ketone group in the macrolide ring.