Abstract
An efficient formal synthesis of (±)-cycloclavine is achieved in seven steps and 27% overall yield from the known 2-(4-bromo-1-tosyl-1H-indol-3-yl)acetaldehyde. Key features include an iron(III)-catalyzed aza-Cope-Mannich cyclization and an intramolecular Heck reaction or a self-terminating 6-exo-trig aryl radical-alkene cyclization.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetaldehyde / analogs & derivatives*
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Acetaldehyde / chemistry
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Catalysis
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Cyclization
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Indole Alkaloids / chemical synthesis*
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Indole Alkaloids / chemistry
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Indoles / chemistry*
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Iron / chemistry
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Molecular Structure
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Stereoisomerism
Substances
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2-(4-bromo-1-tosyl-1H-indol-3-yl)acetaldehy
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Indole Alkaloids
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Indoles
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cycloclavine
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Iron
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Acetaldehyde