Acid-induced rearrangement of epoxygermacranolides: synthesis of furanoheliangolides and cadinanes from nobilin
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4101751
Author(s) De Mieri, M.; Smiesko, M.; Ismajili, I.; Kaiser, M.; Hamburger, M.
Author(s) at UniBasel Hamburger, Matthias
de Mieri, Maria
Smiesko, Martin
Kaiser, Marcel
Year 2017
Title Acid-induced rearrangement of epoxygermacranolides: synthesis of furanoheliangolides and cadinanes from nobilin
Journal Molecules
Volume 22
Number 12
Pages / Article-Number E2252
Abstract The acid-induced rearrangement of three epoxyderivatives of nobilin 1, the most abundant sesquiterpene lactone in Anthemisnobilis flowers, was investigated. From the 1,10-epoxyderivative 2, furanoheliangolide 5 was obtained, while the 4,5-epoxy group of 3 did not react. Conversely, when the 3-hydroxy function of nobilin was acetylated (12), the 4,5-epoxy derivative did cyclize into cadinanes (15 and 16) under Lewis acid catalysis. The reactivity of the 4,5- and 1,10-epoxy derivatives of nobilin (2 and 3) was compared with that of parthenolide, and rationalized on the basis of quantum chemical calculations. All isolated reaction products were fully characterized by spectroscopic and computational methods, and their in vitro anti-protozoal activity was evaluated. The paper could provide new insights into the biosynthesis of this class of natural products.
Publisher MDPI
ISSN/ISBN 1420-3049
edoc-URL http://edoc.unibas.ch/58302/
Full Text on edoc No
Digital Object Identifier DOI 10.3390/molecules22122252
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/29258233
ISI-Number WOS:000419242400214
Document type (ISI) Journal Article
 
   

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