Enantioselective synthesis of a PKC inhibitor via catalytic C-H bond activation.
[reaction: see text] The syntheses of two biologically active molecules possessing dihydropyrroloindole cores (1 and 2) were completed using rhodium-catalyzed imine-directed C-H bond functionalization, with the second of these molecules containing a stereocenter that can be set with 90% ee during cyclization using chiral nonracemic phosphoramidite ligands. Catalytic decarbonylation and direct indole/maleimide coupling provide efficient access to 2.
Wilson
Rebecca M
RM
Department of Chemistry and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, University of California, Berkeley, California 94720, USA.
Thalji
Reema K
RK
Bergman
Robert G
RG
Ellman
Jonathan A
JA
D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011493:Protein Kinase C / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D007211:Indoles; D011493:Protein Kinase C