Skeletal Modification of Tryptophan Using Cyclic Diaryliodonium Salts via Palladium-Catalyzed Cascade π-Extended Annulative Dual C2-H/N-H Arylation
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Updated: Oct 31, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Sowmya B Udayakumar1,2, Kiranmai Nayani1,2
1Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad500007, India.
Abstract:
We have demonstrated an efficient Pd-catalyzed annulative dual C2-H/N-H arylation reaction involving modification of the tryptophan indole skeleton to phenanthridinyl indole. This is an operationally simple and ligand-free strategy that was extended to biologically important indole derivatives and tryptophan-containing short peptides to deliver a diverse unnatural phenanthridinyl indole-tethered peptide with good efficiency. Notably, the method demonstrated good tolerance for N- and C-terminal protecting groups as well as for the side-chain functionalities of other amino acids.
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