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Updated: Jun 8, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Chiral spherical aromatic amides: one-step synthesis and their stereochemical/chiroptical properties
Daiki Koike1, Hyuma Masu2, Shoko Kikkawa1
1Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan. isao.azumaya@phar.toho-u.ac.jp.
Abstract:
Macrocyclic aromatic amides 2, in which the meta-positions of all four benzene rings are linked by tertiary amide bonds, were successfully synthesized by a one-step condensation reaction of two monomers using dichlorotriphenylphosphorane or triphenylphosphine/hexachloroethane (dehydration-condensation reagents for carboxy and amino groups), or LiHMDS (aminolysis for esters) as coupling reagents. Single crystal X-ray analyses of the N-methyl and N-ethyl derivatives were performed and revealed that each compound adopted a spherical structure with chirality because of the fixed axis rotation and combined polarity of the amide bonds. Enantiomers of each spherical macrocycle were separated by chiral column chromatography and showed mirror-imaged CD spectra to each other.
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