ChemInform Abstract: Asymmetric Synthesis of (-)-(R)-Pyrrolam A Starting from (S)-Malic Acid.
Abstract
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ChemInform Abstract
Key steps in the asymmetric synthesis of the title alkaloid (VI) are the highly regioselective addition of Grignard reagent (II) to the (S)-malic acid derived imide (I), followed by highly diastereoselective reduction of hydroxy derivative (III) to provide trans-pyrrolidinone (IV) in good yield. Suitable deprotection—protection sequence then affords the ditosylate (V), which in the presence of NaH undergoes a tandem tosic acid elimination—intramolecular N-substitution to give the title alkaloid (VI).
