Stereochemistry of the roridins. Diastereomers of roridin E.
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.
Jarvis
B B
BB
Department of Chemistry and Biochemistry, and Joint Institute for Food Safety and Nutrition, University of Maryland, College Park, Maryland 20742, USA. bj6@umail.umd.edu
Wang
S
S
D018360:Crystallography, X-Ray; D005658:Fungi / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D014255:Trichothecenes / Q000737:chemistry
D014255:Trichothecenes; C003797:roridin E