Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 18, Pages 6754-6762Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja502744a
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Funding
- CICYT [CTQ2012-30930]
- Generalitat de Catalunya [2009SGR1024]
- Institute for Research in Biomedicine (IRB Barcelona)
- MEC
- ESF
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The marine environment is a rich source of metabolites with potential therapeutic properties and applications for humans. Here we describe the first isolation, solid-phase total synthesis, and full structural assignment of a new class of cyclodepsipeptides from the Madagascan sponge Ecionemia acervus that shows in vitro cytotoxic activities at submicromolar concentrations. Seven structures belonging to a new family of compounds, given the general name stellatolides, were characterized. The sequence and stereochemistry of all the amino acids in these molecules were established by a combination of spectroscopic analysis, chemical degradation, and derivatization studies. Furthermore, the complete structure of stellatolide A was confirmed by an efficient solid-phase method for the first total synthesis and the full structural assignment of this molecule, including the asymmetric synthesis of the unique beta-hydroxy acid moiety (Z)-3-hydroxy-6,8-dimethylnon-4-enoic acid.
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