Abstract
A total synthesis of the racemic natural product tylophorine [(+/-)-1] has been demonstrated using the palladium-catalyzed carboamination method developed by Wolfe and co-workers. In this case, an electron-rich aryl bromide 18 was prepared in four steps and subjected to palladium-catalyzed Wolfe carboamination conditions with olefinic carbamate 7 to provide the racemic 2-(arylmethyl)pyrrolidine (+/-)-19 in good yield and was further elaborated to racemic tylophorine. This application of the Wolfe carboamination protocol as a key step to construct a natural product provides further evidence of the utility of the method.
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Alkenes / chemistry
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Amination
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Antineoplastic Agents, Phytogenic / chemical synthesis*
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Antineoplastic Agents, Phytogenic / chemistry
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Carbamates / chemistry*
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Catalysis
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Hydrocarbons, Brominated / chemistry
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Hydrocarbons, Cyclic / chemistry
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Indolizines / chemical synthesis*
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Indolizines / chemistry
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Models, Chemical
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Palladium / chemistry*
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Phenanthrenes / chemical synthesis*
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Phenanthrenes / chemistry
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Pyrrolidines / chemistry
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Stereoisomerism
Substances
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Alkaloids
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Alkenes
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Antineoplastic Agents, Phytogenic
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Carbamates
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Hydrocarbons, Brominated
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Hydrocarbons, Cyclic
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Indolizines
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Phenanthrenes
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Pyrrolidines
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Palladium
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tylophorine