title: Enantioselective synthesis of a PKC inhibitor via catalytic C-H bond activation.
abstract: [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.
authors.affiliation: Department of Chemistry and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, University of California, Berkeley, California 94720, USA.
authors.forename: Rebecca M
authors.initials: RM
authors.lastname: Wilson
authors.forename: Reema K
authors.initials: RK
authors.lastname: Thalji
authors.forename: Robert G
authors.initials: RG
authors.lastname: Bergman
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman
mesh_terms: 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
chemical_list: D007211:Indoles; D011493:Protein Kinase C