Publication
Title
On the determination of the stereochemistry of semisynthetic natural product analogues using chiroptical spectroscopy : desulfurization of epidithiodioxopiperazine fungal metabolites
Author
Abstract
Isolation and semisynthetic modification of the fungal metabolite chaetocin gave access to a desulfurized analogue of this natural product. Detailed chiroptical studies, comparing experimentally obtained optical rotation values, electronic circular dichroism spectra, and vibrational circular dichroism spectra to computationally simulated ones, reveal the desulfurization of chaetocin to unambiguously proceed with retention of configuration. Consideration of the plausible mechanisms for this process highlighted inconsistencies in the stereochemical assignment of related molecules in the literature. This in turn allowed the stereochemical reassignment of the natural product analogue dethiodehydrogliotoxin.
Language
English
Source (journal)
Chemistry: a European journal. - Weinheim
Publication
Weinheim : 2011
ISSN
0947-6539
Volume/pages
17:42(2011), p. 11868-11875
ISI
000297314100024
Full text (Publishers DOI)
Full text (publishers version - intranet only)
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 07.02.2012
Last edited 25.05.2017
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