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Title
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Dearomative spirocyclization of tryptamine-derived isocyanides via iron-catalyzed carbene transfer
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Author
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Abstract
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| 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. |
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Language
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English
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Source (journal)
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The journal of organic chemistry. - Washington, D.C., 1936, currens
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Publication
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Washington, D.C.
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2023
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ISSN
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0022-3263
[print]
1520-6904
[online]
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DOI
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10.1021/ACS.JOC.3C02160
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Volume/pages
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88
:24
(2023)
, p. 17345-17355
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ISI
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001142998900001
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Pubmed ID
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38048350
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Full text (Publisher's DOI)
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Full text (open access)
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