C-2 functionalization of indoles with xanthate-lactam derivatives by radical-oxidative coupling, an approach to <i>Aspidosperma</i> alkaloids

The C-2 functionalization of various indole derivatives <i>via</i> radical-oxidative coupling is presented. The xanthate precursors utilized as alkylating agents are derived from two distinct lactams, which are of considerable significance due to their presence in numerous monoterpenoid indole alkaloids, such as <i>Aspidosperma</i> and ibophyllidine types. The synthesis of 1,2-dehydroaspidospermidine exemplifies the application of this methodology.

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Journal
RSC Advances
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ra01600b
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

C-2 functionalization of indoles with xanthate-lactam derivatives by radical-oxidative coupling, an approach to Aspidosperma alkaloids

Manuel Pastrana Restrepo, Luis D. Miranda
RSC Advances
Catalytic C–H Functionalization Methods
article

C-2 functionalization of indoles with xanthate-lactam derivatives by radical-oxidative coupling, an approach to Aspidosperma alkaloids

Manuel Pastrana Restrepo, Luis D. Miranda
article en

Abstract

The C-2 functionalization of various indole derivatives <i>via</i> radical-oxidative coupling is presented. The xanthate precursors utilized as alkylating agents are derived from two distinct lactams, which are of considerable significance due to their presence in numerous monoterpenoid indole alkaloids, such as <i>Aspidosperma</i> and ibophyllidine types. The synthesis of 1,2-dehydroaspidospermidine exemplifies the application of this methodology.

RSC AdvancesVol. 15(31)
Universidad Nacional Autónoma de México (MX)
Consejo Nacional de Ciencia y Tecnología, Dirección General de Asuntos del Personal Académico, Universidad Nacional Autónoma de México
Openalex Percentile: Top 87%
Catalytic C–H Functionalization Methods
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