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Synthesis 2020; 52(22): 3420-3426
DOI: 10.1055/s-0040-1707279
DOI: 10.1055/s-0040-1707279
special topic
Synthesis in Industry
Synthesis of an Azabicyclo[3.1.0]hexanone-Containing Inhibitor of NF-κΒ Inducing Kinase via Catalytic C–H Activation
This work was supported by Genentech (a member of the Roche group).


Abstract
The synthesis of an azabicyclo[3.1.0]hexanone-containing inhibitor of the nuclear factor-κB inducing kinase (NIK) is reported. The initial route to this compound was streamlined from 13 to 7 linear steps through the use of a catalytic, enantioselective C–H activation step. A procedure for lactam oxidation was identified that avoided use of peroxides on scale. These synthetic improvements allowed for the synthesis of multigram quantities of the desired NIK inhibitor for in vivo profiling.
Key words
C–H activation - NIK inhibitor - enantioselective - azabicyclo-[3.1.0]hexanone - nuclear factor-κB - medicinal chemistrySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707279.
- Supporting Information
Publikationsverlauf
Eingereicht: 28. Juli 2020
Angenommen: 12. August 2020
Artikel online veröffentlicht:
15. September 2020
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