Abstract
[Chemical reaction: see text] A modular total synthesis of lamellarin D, a marine alkaloid with potent cytotoxic as well as topoisomerase I inhibition properties, has been accomplished. A sequential and regioselective bromination/Suzuki cross-coupling procedure was applied for the introduction of aryl groups at positions 1 and 2 of scaffold 1. Microwave-assisted 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) oxidation to yield pyrroloisoquinoline 15, followed by phenol group deprotection and subsequent lactonization, gave lamellarin D (18% in eight steps from 1).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids
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Coumarins / chemical synthesis*
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Coumarins / chemistry
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Dioxanes
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Indicators and Reagents
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Isoquinolines / chemical synthesis*
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Isoquinolines / chemistry
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Models, Molecular
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Topoisomerase I Inhibitors
Substances
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Alkaloids
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Coumarins
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Dioxanes
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Enzyme Inhibitors
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Heterocyclic Compounds, 4 or More Rings
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Indicators and Reagents
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Isoquinolines
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Topoisomerase I Inhibitors
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lamellarin D
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1,4-dioxane