Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 42, Pages 11930-11934Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201101139
Keywords
biosynthesis; glaciapyrrol A; heterocycles; natural products; terpenes
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Funding
- Deutsche Forschungsgemeinschaft (DFG)
- Emmy Noether fellowship
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The total syntheses of the structurally unique and moderately cytotoxic pyrrolosesquiterpenoid glaciapyrrol A that has been isolated from a marine streptomycete by Macherla et al.([1]) and of seven of its stereoisomers have been performed from geraniol or nerol, respectively, using a known diastereoselective Ru-catalysed approach for the synthesis of tetrahydrofurans previously reported by Stark and co-workers.([5]) Comparison of H-1 and C-13 NMR data unambiguously clarified the relative configuration of natural glaciapyrrol A that was previously only partly solved from the available NMR data. An enantioselective synthesis was carried out resulting in the unnatural enantiomer (11S,12R,15R)-(-)-glaciapyrrol A. These data establish the absolute configuration of the natural product as (11R,12S,15S)-(+)-glaciapyrrol A.
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