Abstract
The first total enantioselective synthesis of plakotenin is described. This marine natural product was isolated from an Okinawan sponge of the genus Plakortis and shows potent biological activity against several cancerous cell lines. A biomimetic intramolecular Diels-Alder reaction served as a key step in the total synthesis. The synthesis proves the relative and absolute stereochemistry of natural plakotenin.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry*
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Antineoplastic Agents / metabolism
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Antineoplastic Agents / pharmacology
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Carboxylic Acids / chemical synthesis*
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Carboxylic Acids / chemistry*
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Carboxylic Acids / metabolism
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Carboxylic Acids / pharmacology
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Cell Line, Tumor
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Plakortis / metabolism*
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Stereoisomerism
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Substrate Specificity
Substances
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Antineoplastic Agents
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Carboxylic Acids
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plakotenin