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The Absolute Configuration of the Pyrrolosesquiterpenoid Glaciapyrrol A
Author(s) -
Riclea Ramona,
Dickschat Jeroen S.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101139
Subject(s) - absolute configuration , geraniol , enantioselective synthesis , enantiomer , stereochemistry , nerol , natural product , chemistry , total synthesis , absolute (philosophy) , organic chemistry , catalysis , philosophy , epistemology , chromatography , essential oil
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 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 (11 S ,12 R ,15 R )‐(−)‐glaciapyrrol A. These data establish the absolute configuration of the natural product as (11 R ,12 S ,15 S )‐(+)‐glaciapyrrol A.
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