Total synthesis of carbazoquinocin C: application of the o-benzannulation of Fischer carbene complexes to carbazole-3,4-quinone alkaloids.

@article{Rawat2004TotalSO,
  title={Total synthesis of carbazoquinocin C: application of the o-benzannulation of Fischer carbene complexes to carbazole-3,4-quinone alkaloids.},
  author={M. Rawat and W. Wulff},
  journal={Organic letters},
  year={2004},
  volume={6 3},
  pages={
          329-32
        }
}
  • M. Rawat, W. Wulff
  • Published 2004
  • Chemistry, Medicine
  • Organic letters
    • [reaction: see text] The photoinduced o-benzannulation of 3-(2-vinyl)indolylcarbene complexes provides a direct route to carbazole derivatives that are oxygenated in the 3- and 4-positions. This reaction is quite efficient and provides for a unique synthesis of the lipid peroxidation inhibitor carbazoquinocin C. 
    View on PubMed
    www2.chemistry.msu.edu
    48 Citations
    Background Citations
    2

    Topics from this paper

    Explore Further: Topics Discussed in This Paper

    48 Citations
    Citation Type

    Citation Type

    An efficient synthesis of carbazoles from PtCl(2)-catalyzed cyclization of 1-(indol-2-yl)-2,3-allenols.
    • 78
    • PDF
    One-pot synthesis of carbazoles from indoles via a metal free benzannulation
    • 4
    Anionic [4+2] cycloaddition strategy in the regiospecific synthesis of carbazoles: formal synthesis of ellipticine and murrayaquinone A
    • 38
    Formal [4 + 2] benzannulation of 2-alkenyl indoles with aldehydes: a route to structurally diverse carbazoles and bis-carbazoles.
    • 5
    • PDF
    Regioselective synthesis of 1-hydroxycarbazoles via anionic [4+2] cycloaddition of furoindolones : a short synthesis of murrayafoline-A
    • 12
    A new approach to 1-substituted β-carbolines and isoquinolines utilizing tributyl[(Z)-2-ethoxyvinyl]stannane as a C-3,C-4 building block
    • 14
    Benzannulation of 2-Alkenylindoles using Aldehydes by Sequential Triple-Relay Catalysis: A Route to Carbazoles and Carbazole Alkaloids
    • 21
    High throughput synthesis of diverse 2,5-disubstituted indoles using titanium carbenoids bearing boronate functionality
    • 7
    • PDF
    Palladium catalyzed dual C-H functionalization of indoles with cyclic diaryliodoniums, an approach to ring fused carbazole derivatives.
    • 34
    • PDF
    Syntheses of vinylindoles via a Brønsted acid catalyzed highly regio- and stereoselective cis-hydroarylation of ynamides ☆
    • 48

    References

    SHOWING 1-10 OF 23 REFERENCES
    Benzannulation reactions of Fischer carbene complexes for the synthesis of indolocarbazoles
    • 53
    Indoloquinones, part 5. Palladium-catalyzed total synthesis of the potent lipid peroxidation inhibitor carbazoquinocin C
    • 49
    Indoloquinones, Part 7. Total Synthesis of the Potent Lipid Peroxidation Inhibitor Carbazoquinocin C by an Intramolecular Palladium-Catalyzed Oxidative Coupling of an Anilino-1,4-benzoquinone
    • 52
    • PDF
    Synthesis and biological evaluation of structural variants of carbazoquinocin C
    • 5
    An efficient method for the N-debenzylation of aromatic heterocycles
    • 64
    Aminobenzannulation via photocyclization reactions of chromium dienyl(amino)carbene complexes. Synthesis of o-amino aromatic alcohols
    • 37
    Synthetic Studies on Indoles and Related Compounds. XXVI. The Debenzylation of Protected Indole Nitrogen with Aluminum Chloride. (2)
    • 42
    Transition metal complexes in organic synthesis, part 59.(1) First enantioselective total synthesis of lavanduquinocin, a potent neuronal cell protecting substance from streptomyces viridochromogenes.
    • 10
    Transition metal complexes in organic synthesis, part 37.1 convergent iron-mediated total synthesis of the potent lipid peroxidation inhibitor carbazoquinocin C
    • 32
    Transition metal complexes in organic synthesis. Part 58: First enantioselective total synthesis of the potent neuronal cell protecting substance carquinostatin A from ( R )-propene oxide
    • 41