Enantioselective Synthesis of a PKC Inhibitor via Catalytic C-HBond Activation

Journal Article · Sun Feb 26 00:00:00 EST 2006 · Organic Letters

DOI:https://doi.org/10.1021/ol060485h· OSTI ID:908170

Wilson, Rebecca M; Thalji, Reema K; Bergman, Robert G; Ellman, Jonathan A

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.

• Research Organization: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
• Sponsoring Organization: USDOE Director. Office of Science. Office of Basic EnergySciences. Chemical Sciences Geosciences and Biosciences Division; National Institutes of Health Grant GM069559
• DOE Contract Number: DE-AC02-05CH11231
• OSTI ID: 908170
• Report Number(s): LBNL-59469; XX5305; R&D Project: 402101; BnR: KC0302010; TRN: US200722%%516
• Journal Information: Organic Letters, Vol. 8, Issue 8; Related Information: Journal Publication Date: 2006; ISSN 1523-7060
• Country of Publication: United States
• Language: English

Related Subjects

37
SYNTHESIS
CATALYSIS
MOLECULES
RHODIUM