Concise Synthesis of Pyrrolidine and Indolizidine Alkaloids by a Highly Convergent Three‐Component Reaction

作者: Guillaume Lapointe , Kurt Schenk , Philippe Renaud

DOI: 10.1002/CHEM.201003137

关键词: Reductive aminationOrganic chemistryYield (chemistry)ChemistryPyrrolidineMonomorine ITotal synthesisIndolizidineEnantioselective synthesisRadicalStereochemistry

摘要: The synthesis of pyrrolidine and indolizidine derivatives through radical carboazidation alkenes with alpha-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 three different simple alkaloids, including (+/-)-monomorine I.

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