Abstract
A concise total synthesis of aetheramide A in an overall yield of 4.7% with a longest linear sequence of 15 steps is described. This synthetic strategy features macrocyclization via an intramolecular trapping of acylketene generated from dioxinone precursor, and stereoselective late-stage methylation of β-ketoamide. Aetheramide B could be synthesized via the ester migration of aetheramide A.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-HIV Agents / chemical synthesis*
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Anti-HIV Agents / chemistry
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Anti-HIV Agents / pharmacology
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Carbon-13 Magnetic Resonance Spectroscopy
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Cyclization
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Depsipeptides / chemical synthesis*
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Depsipeptides / chemistry
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Depsipeptides / pharmacology
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Methylation
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Proton Magnetic Resonance Spectroscopy
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Spectrometry, Mass, Electrospray Ionization
Substances
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Anti-HIV Agents
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Depsipeptides
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aetheramide A
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aetheramide B