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Updated: Apr 23, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Total synthesis of (-)-aspergilazine A
Emily M Boyd1, Jonathan Sperry
1School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland, New Zealand.
Abstract:
The total synthesis of (-)-aspergilazine A, an alkaloid possessing a rare N1' to C6 bisindole bond, is described. A palladium-catalyzed N-arylation was used to selectively install the N1'-C6 bond in the presence of three other possible arylation sites. The ligand XPhos displayed a unique capability to efficiently carry out the N-arylation while simultaneously suppressing epimerization of the sensitive C9 stereocenters. This total synthesis has confirmed that aspergilazine A is a dimer of brevianamide F.
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