The absolute configuration of the pyrrolosesquiterpenoid glaciapyrrol A |
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Authors: | Riclea Ramona Dickschat Jeroen S |
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Institution: | Technische Universit?t Braunschweig, Institut für Organische Chemie, Hagenring 30, 38106 Braunschweig (Germany), Fax: (+49)?531‐3915272 |
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Abstract: | 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. 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. Comparison of (1)H and (13)C 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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Keywords: | biosynthesis glaciapyrrol A heterocycles natural products terpenes |
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