Abstract
The synthesis of pyrrolidine and indolizidine derivatives through radical carboazidation of alkenes with α-iodoketones, followed by reductive amination, is described. When properly substituted, further lactamization afforded pyrrolizidinones in good yield. This carboazidation/reductive amination sequence was efficiently applied to the total synthesis of three different simple alkaloids, including (±)-monomorine I.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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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Amination
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Crystallography, X-Ray
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Free Radicals / chemistry
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Indolizidines / chemical synthesis
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Indolizidines / chemistry*
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Indolizines / chemical synthesis
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Indolizines / chemistry
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Ketones / chemistry
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Molecular Conformation
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Pyrrolidines / chemical synthesis
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Pyrrolidines / chemistry*
Substances
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Alkaloids
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Free Radicals
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Indolizidines
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Indolizines
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Ketones
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Pyrrolidines
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monomorine
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pyrrolidine