Abstract
This account describes the development of a Diels-Alder-based
methodology towards highly functionalized dihydronaphthalenamines,
and their conversion into indoles through a modified Plieninger
procedure. Applications towards the total synthesis of indole-containing
natural products will be presented.
1 Introduction
2 Synthesis of Indoles via Diels-Alder Cycloadditions/Plieninger
Indolization
2.1 High Pressure Diels-Alder Cycloadditions of Quinone Imine
Ketals (QIKs)
2.2 Thermal Diels-Alder Cycloadditions of QIKs
2.3 Development of a Modified Plieninger Protocol
2.4 Diels-Alder Cycloadditions/Indolization
of p -Benzoquinone Monoimines
3 Applications to Natural Products Synthesis
3.1 Ergot Alkaloids: Chanoclavine I (Plieninger)
3.2 Rivularins (Maehr)
3.3 Polyalkylated Indoles: Herbindoles and Trikentrins (Kerr)
3.4 Tremorgenic Indole Terpenoids: Lolicine Western Hemisphere
(Kerr)
3.5 Antitumor Agents: Yatakemycin (Boger) and CC-1065 (Kraus,
Kerr)
3.6 Antimalarials: Decursivine (Kerr)
3.7 Carbazole Natural Products: The Clausamines and Eustifolines
(Kerr)
4 Summary and Outlook
Key words
cycloadditions - Diels-Alder reaction - indoles - natural products - total synthesis
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