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

Abstract

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:
; ; ;
Publication Date:
Research Org.:
Ernest Orlando Lawrence Berkeley NationalLaboratory, Berkeley, CA (US)
Sponsoring Org.:
USDOE Director. Office of Science. Office of Basic EnergySciences. Chemical Sciences Geosciences and Biosciences Division; National Institutes of Health Grant GM069559
OSTI Identifier:
908170
Report Number(s):
LBNL-59469
Journal ID: ISSN 1523-7060; XX5305; R&D Project: 402101; BnR: KC0302010; TRN: US200722%%516
DOE Contract Number:  
DE-AC02-05CH11231
Resource Type:
Journal Article
Resource Relation:
Journal Name: Organic Letters; Journal Volume: 8; Journal Issue: 8; Related Information: Journal Publication Date: 2006
Country of Publication:
United States
Language:
English
Subject:
37; SYNTHESIS; CATALYSIS; MOLECULES; RHODIUM

Citation Formats

Wilson, Rebecca M., Thalji, Reema K., Bergman, Robert G., and Ellman,Jonathan A. Enantioselective Synthesis of a PKC Inhibitor via Catalytic C-HBond Activation. United States: N. p., 2006. Web. doi:10.1021/ol060485h.
Wilson, Rebecca M., Thalji, Reema K., Bergman, Robert G., & Ellman,Jonathan A. Enantioselective Synthesis of a PKC Inhibitor via Catalytic C-HBond Activation. United States. doi:10.1021/ol060485h.
Wilson, Rebecca M., Thalji, Reema K., Bergman, Robert G., and Ellman,Jonathan A. Sun . "Enantioselective Synthesis of a PKC Inhibitor via Catalytic C-HBond Activation". United States. doi:10.1021/ol060485h.
@article{osti_908170,
title = {Enantioselective Synthesis of a PKC Inhibitor via Catalytic C-HBond Activation},
author = {Wilson, Rebecca M. and Thalji, Reema K. and Bergman, Robert G. and Ellman,Jonathan A.},
abstractNote = {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.},
doi = {10.1021/ol060485h},
journal = {Organic Letters},
number = 8,
volume = 8,
place = {United States},
year = {Sun Feb 26 00:00:00 EST 2006},
month = {Sun Feb 26 00:00:00 EST 2006}
}