80243-75-0Relevant academic research and scientific papers
STEREOCONTROLLED CONVERSION OF 3,5-DIOXOPYRROLIZIDINE INTO (Z)- AND (E)-5-ACETONYLPYRROLIZIDIN-3-ONES
Takahashi, Kimio,Brossi, Arnold
, p. 835 - 842 (2007/10/02)
Stereocontrolled synthesis of (Z)-5-acetonylpyrrolizidin-3-one (4) and (E)-isomer 5 from 3,5-dioxopyrrolizidine 1 is described.
(E)-5-Hydroxypyrrolizidin-3-one: Versatile Synthon for the Synthesis of 5-Substituted 2-Pyrrolidones and (Z)-3-Alkylpyrrolizidines
Buchs, Peter,Brossi, Arnold,Flippen-Anderson, Judith L.
, p. 719 - 723 (2007/10/02)
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.
