Abstract
An enantioselective synthetic method for (-)-cis-clavicipitic acid (1) was reported. 1 was obtained in 10 steps (99% ee and 20% overall yield) from 1H-indole-3-carboxylic acid methyl ester (9) via asymmetric phase-transfer catalytic alkylation and diastereoselective Pd(II)-catalyzed intramolecular aminocyclization as key steps.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Alkaloids / isolation & purification
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Alkylation
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Azepines / chemical synthesis*
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Azepines / chemistry
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Azepines / isolation & purification
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Catalysis
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Claviceps / chemistry*
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Ergot Alkaloids
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Esters
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Indoles / chemical synthesis*
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Indoles / chemistry
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Indoles / isolation & purification
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Molecular Structure
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Palladium / chemistry
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Phase Transition
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Stereoisomerism
Substances
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Alkaloids
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Azepines
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Ergot Alkaloids
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Esters
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Indoles
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clavicipitic acid
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indole-3-carboxylic acid
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Palladium