Total Synthesis of Phenanthroindolizidines Using Strained Azacyclic Alkynes.
Journal
Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393
Informations de publication
Date de publication:
14 Jul 2023
14 Jul 2023
Historique:
pmc-release:
14
07
2024
medline:
17
7
2023
pubmed:
28
6
2023
entrez:
28
6
2023
Statut:
ppublish
Résumé
We report a concise approach to phenanthroindolizidine alkaloids, wherein strained azacyclic alkynes are intercepted in Pd-catalyzed annulations. Two types of strained intermediates were evaluated: a functionalized piperidyne and a new strained intermediate, an indolizidyne. We show that each can be employed, ultimately allowing access to three natural products: tylophorine, tylocrebine, and isotylocrebine. These efforts demonstrate the successful merger of strained azacyclic alkyne chemistry with transition-metal catalysis for the construction of complex heterocycles.
Identifiants
pubmed: 37379230
doi: 10.1021/acs.orglett.3c01740
pmc: PMC10460089
mid: NIHMS1926231
doi:
Substances chimiques
phenanthroindolizidine
0
Alkynes
0
Transition Elements
0
Phenanthrolines
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
5044-5048Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM139593
Pays : United States
Organisme : NIH HHS
ID : S10 OD028644
Pays : United States
Organisme : NCRR NIH HHS
ID : S10 RR025631
Pays : United States
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