(E)-5-Hydroxypyrrolizidin-3-one: versatile synthon for the synthesis of 5-substituted 2-pyrrolidones and (Z)-3-alkylpyrrolizidines

Abstract

propylanisole and 3-benzyl-2,6-dipropylanisole as a colorless oil.Acknowledgment. We thank the donors of the Petroleum Research Fund, administered by the American Chemical Society, and the BRSG program of the National Institutes of Health for grants in support of this work.

ChemInform Abstract: Synthesis of (.+‐.)‐trans‐2,5‐Dialkylpyrrolidines from the Lukes‐Sorm Dilactam: Efficient Preparation of (.+‐.)‐trans‐2‐Butyl‐5‐heptylpyrrolidine and Analogs Present in Ant Venoms.

“…We report here a versatile synthesis of 2,5-disubstituted ant pyrrolidines from the Lukes-Sorm dilactam 1, already used to prepare 3-alkyl-substituted pyrrolizidines ( = hexahydro-lH-pyrrolizine) [24], by a route which should be amenable to the synthesis of all saturated 2,5-dialkylpyrrolidines so far reported [14] [25]. Dilactam 1 smoothly reacted with Grignard reagents to afford in high yield ketones of type 2 and 3 (Scheme 1 ), which were converted into 2,5-dialkylpyrrolidines by the route described here in detail for the conversion of 2 into 142).…”