Concise Synthesis of Pyrrolidine and Indolizidine Alkaloids by a Highly Convergent Three-Component Reaction
The synthesis of pyrrolidine and indolizidine derivatives through radical carboazidation of 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 synthesis of three different simple alkaloids, including (+/-)-monomorine I.
Keywords: alkaloids ; carboazidation ; iodoketones ; pyrrolidines ; radicals ; Radical Carboazidation ; Asymmetric-Synthesis ; Amphibian Skin ; Azides ; (+)-Monomorine-I ; Pyrrolizidines ; Derivatives ; Reduction ; Chemistry ; Azidation
Record created on 2011-12-16, modified on 2016-08-09