Stereochemistry of the Roridins. Diastereomers of Roridin E

• Published in: Journal of natural products (Washington, D.C.) Vol. 62; no. 9; pp. 1284 - 1289
• Main Authors: Jarvis, Bruce B, Wang, Shengjun
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.09.1999; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Biological and medical sciences; chemical constituents of plants; chemical structure; Chemistry, Medicinal; Crystallography, X-Ray; cultured cells; Fundamental and applied biological sciences. Psychology; Fungi - chemistry; Gas Chromatography-Mass Spectrometry; isomers; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Microbiology; Molecular Structure; Morphology, structure, chemical composition; Mycology; Myrothecium verrucaria; Pharmacology & Pharmacy; Plant Sciences; roridins; Science & Technology; spectral analysis; stereochemistry; Stereoisomerism; Trichothecenes - chemistry; BACCHARIS-CORIDIFOLIA; MACROCYCLIC TRICHOTHECENES; Stereoisomer; Terpenoid; Myrothecium; Mycotoxin; Lactone; Oxygen heterocycle; Macrolide; Trichothecene; Macrocycle; Fungi; Toxin; Microbial origin; Sesquiterpenes; Isolation; Fungi Imperfecti; Diastereomer; Thallophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np990272j

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.