Trends in carbazole synthesis – an update (2013–2023)

Abstract

This review discusses last decade's developments in carbazole synthesis. Aspects of selectivity and functional group tolerance are evaluated, as well as the applicability of such protocols towards the total synthesis of natural products.

Fluorescent carbazole-derived α-amino acids: structural mimics of tryptophan

“…The first stage of this project investigated the development of a concise route to access a focused library of carbazole α-amino acids. 12 Various strategies were considered and it was proposed that the Negishi coupling of halo-substituted carbazoles with an organozinc reagent derived from a β-iodoalanine derivative would allow rapid access to the amino acid targets. 13 Precedent for the use of this type of β-alanine anion reagent, developed by Jackson and co-workers, has been shown with coupling to various halogenated N-heterocycles such as pyridines and N -protected indoles.…”

Synthesizing Chiral Hydrocarbazoles with a Tetrasubstituted Carbon Using Holmium-Catalyzed Enantioselective [4 + 2] Cycloaddition: Mechanistic Insights from Luminescence and DFT Studies

“…Hydrocarbazole is an essential substructure of several biologically active compounds. Strychnine and vinblastine, along with minovincine, are representative compounds, and the development of synthetic methods for these polysubstituted hydrocarbazole skeletons is a crucial research objective . Diels–Alder reaction is one of the most reliable methods of achieving this target (Figure ).…”