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Updated: Sep 14, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Convergent Total Synthesis of Erchinines A and B and Their C20 Epimers
Yong Sun Cho1, Joseph P Tuccinardi1, John L Wood1
1Department of Chemistry and Biochemistry, Baylor University, One Bear Place 97348, Waco, Texas 76798, United States.
Abstract:
The total synthesis of two monoterpenoid indole alkaloids (MIAs), erchinines A and B, is described. Isolated from the plant Ervatamia chinensis, both compounds display antimicrobial activity against Trichophyton rubrum and Bacillus subtilis. Their structures are composed of a unique caged system, bearing a 1,4-diazepine fused oxazolidine moiety and containing three successive N,O-acetals. Key features of the synthesis include the construction of the 2-aza-3-oxobicyclo[2.2.2]octene core via an intramolecular pyridone Diels-Alder reaction and a Zr-mediated bisamide reduction that induces a tandem N,O-acetal forming cascade reaction.
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