(E)-5-Hydroxypyrrolizidin-3-one: Versatile Synthon for the Synthesis of 5-Substituted 2-Pyrrolidones and (Z)-3-Alkylpyrrolizidines

Article abstract of DOI:10.1021/jo00343a023

Carbinol lactam 6 of secured stereochemistry served as a synthon to prepare 5-substituted 2-pyrrolidones and pyrrolizidin-3-ones.The relative stereochemistry of 6 and the dithioketal 13, prepared from the keto lactam 11, was established by single-crystal X-ray analysis.Desulfurization of the dithioketals 13 and 14 afforded the 5-n-propylpyrrolizidin-3-ones 15 and 16.Reduction of lactam 15 with LiAlH4 gave the racemic (Z)-3-n-propylpyrrolizidine (17), an analogue of a substance recently detected in ant species.