Abstract
Keep me skipped: a highly convergent total synthesis of ripostatin B, an inhibitor of the bacterial RNA polymerase, is described. The key steps to construct and avoid isomerization of the skipped triene are a double Stille cross-coupling reaction and a ring-closing metathesis. Furthermore, 15-deoxyripostatin A, a stable and conformationally locked analogue of ripostatin A, was prepared and tested in vivo.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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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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DNA-Directed RNA Polymerases / antagonists & inhibitors*
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DNA-Directed RNA Polymerases / metabolism
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology
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Escherichia coli / drug effects
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Lactones / chemical synthesis*
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Lactones / chemistry
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Lactones / pharmacology
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Myxococcales / enzymology
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Staphylococcus aureus / drug effects
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Stereoisomerism
Substances
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15-deoxyripostatin A
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Anti-Bacterial Agents
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Enzyme Inhibitors
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Lactones
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ripostatin B
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DNA-Directed RNA Polymerases