Abstract
The natural product himastatin has an unusual homodimeric structure that presents a substantial synthetic challenge. We report the concise total synthesis of himastatin from readily accessible precursors, incorporating a final-stage dimerization strategy that was inspired by a detailed consideration of the compound's biogenesis. Combining this approach with a modular synthesis enabled expedient access to more than a dozen designed derivatives of himastatin, including synthetic probes that provide insight into its antibiotic activity.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Bacterial Agents / chemical synthesis
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology
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Bacillus subtilis / drug effects
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Bacillus subtilis / ultrastructure
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Cell Membrane / drug effects
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Cell Membrane / ultrastructure
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Chemistry Techniques, Synthetic*
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Dimerization
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Molecular Structure
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Peptides, Cyclic / chemical synthesis
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Peptides, Cyclic / chemistry
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Peptides, Cyclic / pharmacology
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Stereoisomerism
Substances
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Anti-Bacterial Agents
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Peptides, Cyclic
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himastatin