Abstract
A new asymmetric total synthesis of a phenanthroindolizidine alkaloid (S)-tylophorine is reported, which features a catalytic asymmetric allylation of aldehydes and an unexpected one-pot DMAP promoted isocyanate formation and Lewis acid catalyzed intramolecular cyclization reaction. In addition, White's direct C-H oxidation catalyst system converting monosubstituted olefins to linear allylic acetates was also employed for late-stage transformation.
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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Catalysis
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Chemistry, Organic / methods*
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Cyclization
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Indolizines / chemical synthesis*
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Indolizines / chemistry
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Isocyanates / chemical synthesis*
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Isocyanates / chemistry
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Lewis Acids / chemistry*
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Phenanthrenes / chemical synthesis*
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Phenanthrenes / chemistry
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Phenanthrolines / chemistry
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Pyridines / chemistry*
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Stereoisomerism
Substances
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4-(dimethylamine)pyridine
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Alkaloids
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Indolizines
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Isocyanates
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Lewis Acids
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Phenanthrenes
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Phenanthrolines
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Pyridines
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phenanthroindolizidine
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tylophorine