Abstract
The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R)-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative cleavage-oxidation sequence as the key steps. The activity of these natural products, and natural product analogues was also assessed against Mycobacterium tuberculosis in vitro.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Infective Agents / chemical synthesis
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Anti-Infective Agents / chemistry
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Anti-Infective Agents / pharmacology
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Biological Products / chemical synthesis*
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Biological Products / chemistry*
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Biological Products / pharmacology
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Lauric Acids / chemical synthesis
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Lauric Acids / chemistry
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Lauric Acids / pharmacology
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Lipopeptides / chemical synthesis*
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Lipopeptides / chemistry*
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Lipopeptides / pharmacology
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Mycobacterium tuberculosis / drug effects
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Stereoisomerism
Substances
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Anti-Infective Agents
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Biological Products
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Lauric Acids
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Lipopeptides
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fellutamide B
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lauric acid