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Updated: Apr 29, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
An efficient synthesis strategy to the core structure of 6-5-6-5-6-membered epipolythiodiketopiperazines
Hannes F Zipfel1, Erick M Carreira
1Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich , CH-8093 Zürich, Switzerland.
Abstract:
A concise route to the core structure 1 of 6-5-6-5-6-membered epipolythiodiketopiperazines is described. The strategy relies on construction of the pyrrolines by double nucleophilic opening of a bis(oxabicyclo[2.2.1]heptene) 2, obtained after bidirectional condensation of N,N'-diacetyldiketopiperazine (4) with aldehyde 3.
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