Abstract
A concise, eight-step total synthesis of (-)-indolactam V, a nanomolar agonist of protein kinase C, is reported. The synthesis relies upon an efficient copper-catalyzed amino acid arylation to establish the indole C4-nitrogen bond. This cross-coupling method is applicable to a range of hydrophobic amino acids, providing a platform for further diversification of indolactam alkaloid scaffolds and studies on their potent biological activity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Humans
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Indoles / chemical synthesis*
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Indoles / chemistry
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Indoles / pharmacology
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Lactams / chemical synthesis*
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Lactams / chemistry
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Lactams / pharmacology
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Molecular Structure
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Protein Kinase C / metabolism
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Protein Kinase Inhibitors / chemical synthesis*
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Protein Kinase Inhibitors / chemistry
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Protein Kinase Inhibitors / pharmacology
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Stereoisomerism
Substances
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Indoles
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Lactams
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Protein Kinase Inhibitors
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indolactam V
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Protein Kinase C