A Homo-Mannich Reaction Strategy Enables Collective Access to Ibophyllidine, Aspidosperma, Kopsia, and Melodinus Alkaloids.
Alkaloids
Cyclopropanol
Homo-Mannich Reaction
Natural Products
Total Synthesis
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
11 09 2023
11 09 2023
Historique:
received:
24
05
2023
medline:
7
9
2023
pubmed:
25
7
2023
entrez:
25
7
2023
Statut:
ppublish
Résumé
We report here a homo-Mannich reaction of cyclopropanol with an iminium ion, generated by an asymmetric allylic dearomatization of indole, to construct a tricyclic hydrocarbazole core, which is shared by a variety of monoterpenoid indole alkaloids across families. Through this approach, an all-carbon quaternary stereogenic center as well as an allyl and a ketone group were installed. Using this functionalized hydrocarbazole as the structural platform, D ring and E rings of different sizes (i.e., five-, six-, and seven-membered) were successively or simultaneously assembled, leading to a collective asymmetric synthesis of seven alkaloids belonging to the ibophyllidine, Aspidosperma, Kopsia, and Melodinus alkaloid families.
Identifiants
pubmed: 37490018
doi: 10.1002/anie.202307286
doi:
Substances chimiques
Secologanin Tryptamine Alkaloids
0
Indole Alkaloids
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202307286Informations de copyright
© 2023 Wiley-VCH GmbH.
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