@article{bf5a43cae8664077a1c856523b3cde7c,
title = "Dearomative Spirocyclization of Tryptamine-Derived Isocyanides via Iron-Catalyzed Carbene Transfer",
abstract = "Tryptamine-derived isocyanides are valuable building blocks in the construction of spirocyclic indolenines and indolines via dearomatization of the indole moiety. We report the Bu4N[Fe(CO)3NO]-catalyzed carbene transfer of α-diazo esters to 3-(2-isocyanoethyl)indoles, leading to ketenimine intermediates that undergo spontaneous dearomative spirocyclization. The utility of this iron-catalyzed carbene transfer/spirocyclization cascade was demonstrated by its use as a key step in the formal total synthesis of monoterpenoid indole alkaloids (±)-aspidofractinine, (±)-limaspermidine, (±)-aspidospermidine, and (±)-17-demethoxy-N-acetylcylindrocarine.",
author = "Roose, {Thomas R.} and Finn McSorley and Bryan Groenhuijzen and Saya, {Jordy M.} and Maes, {Bert U. W.} and Orr{\`u}, {Romano V. A.} and Eelco Ruijter",
year = "2023",
month = dec,
day = "15",
doi = "10.1021/acs.joc.3c02160",
language = "English",
volume = "88",
pages = "17345--17355",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "24",
}