This work demonstrates the synthesis of α-glucosidase-active indole alkaloids in tryptophane derivatives, suggesting new pathways for functionalization.
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 10 R 3-indolylmethyl benzodiazepine-2,5-dione unit at C-3 of the C4-C7 prenylated indoles. Methods of direct and indirect prenylation of indole and tryptophane were explored. Different approaches were adopted for functionalization of C4-C7 prenyl indoles at C3 using Negishi cross-coupling methods. The asperdinones are among the rare tryptophane-derived indole alkaloids which appear to have undergone epimerization due to genetic alteration of specific gene clusters that code for a C10 R configuration
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Devarajappa et al. (2025) studied this question.
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