Approaches to the Synthesis of the Antitumor Pyridocarbazole Alkaloids

All articles of this category A personal account of the author's several approaches to the synthesis of the antitumor plant alkaloid ellipticine (5,11-dimethyl-6 H -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