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Updated: Jan 8, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Total synthesis of asperdinones B, C, D, E and terezine D
Ravi Devarajappa1, Stephen Hanessian1,2
1Department of Chemistry, Université de Montréal, Station Centre-Ville, C.P. 6128, Montreal, QC, H3C 3J7, Canada.
Abstract:
The total synthesis of new members of prenylated indole alkaloids exhibiting α-glucosidase activity is described. Asperdinones B, C, D, and E are characterized by the presence of a (3R)-3-indolylmethylbenzodiazepine-2,5-dione unit at C-3 of C4-C7 prenylated indoles. Methods of direct and indirect prenylation of indole and tryptophan were explored. Different approaches were adopted for the functionalization of C4-C7 prenylindoles at C-3 using Negishi cross-coupling methods. The asperdinones are among the rare tryptophan-derived indole alkaloids which appear to have undergone epimerization due to genetic alteration of specific gene clusters that code for a (3R) configuration.
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