Abstract
A total synthesis of denbinobin (1) in seven steps with an overall yield of 10% is reported. This synthesis used an FeCl3-assisted cyclization of stilbene to form a phenanthrene. The poor yields of the decarboxylation and methoxylation steps were improved upon to become essentially quantitative. This scalable methodology was carried out using ordinary laboratory reagents.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anthraquinones / chemical synthesis*
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Anthraquinones / chemistry
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Anthraquinones / pharmacology
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Antineoplastic Agents, Phytogenic / chemical synthesis*
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / pharmacology
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Apoptosis / drug effects
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Chlorides / chemistry
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Cyclization
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Ferric Compounds / chemistry
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Molecular Structure
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Phenanthrenes / chemical synthesis*
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Phenanthrenes / chemistry
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Phenanthrenes / pharmacology
Substances
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Anthraquinones
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Antineoplastic Agents, Phytogenic
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Chlorides
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Ferric Compounds
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Phenanthrenes
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denbinobin
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ferric chloride