Publication
Title
Dearomative spirocyclization of tryptamine-derived isocyanides via iron-catalyzed carbene transfer
Author
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.
Language
English
Source (journal)
The journal of organic chemistry. - Washington, D.C., 1936, currens
Publication
Washington, D.C. : 2023
ISSN
0022-3263 [print]
1520-6904 [online]
DOI
10.1021/ACS.JOC.3C02160
Volume/pages
88 :24 (2023) , p. 17345-17355
ISI
001142998900001
Pubmed ID
38048350
Full text (Publisher's DOI)
Full text (open access)
UAntwerpen
Faculty/Department
Research group
Project info
Synthesis of heterocycles via tandem reactions involving in situ generated ketenimines.
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Record
Identifier
Creation 12.12.2023
Last edited 01.02.2024
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