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Synlett 1991; 1991(5): 289-300
DOI: 10.1055/s-1991-20733
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Approaches to the Synthesis of the Antitumor Pyridocarbazole Alkaloids

Gordon W. Gribble*
  • *Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA
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Publication Date:
07 March 2002 (online)

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A personal account of the author's several approaches to the synthesis of the antitumor plant alkaloid ellipticine (5,11-dimethyl-6H-pyrido[4,3-b]carbazole) and related pyridocarbazoles is presented. 1. Introduction 1.1. Restricted Nitrogen Inversion 1.2. Through-Space Hydrogen-Fluorine Coupling 1.3. Polycyclic Aromatic Hydrocarbon Synthesis 2. Diels-Alder Approaches to Pyridocarbazoles 2.1. Pyrrolo[3,4-b]indoles 2.2. Furo[3,4-b]indoles 2.2.1. Synthesis of Furo[3,4-b]indoles 2.2.2. [4+2] Cycloaddition Reactions of Furo[3,4-b]indoles 2.2.3. Synthesis of Ellipticine 3. Metalation/Acylation Approaches to Pyridocarbazoles 3.1. Indole Dianions 3.2. Synthesis of Ellipticine 3.3. Synthesis of Other Pyridocarbazoles 4. Concluding Remarks

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