Synthesis of Highly Substituted
Indoles via Diels-Alder/Plieninger Indolization
Sequence: Applications in Total Synthesis

Katarina Sapeta; Terry P. Lebold; Michael A. Kerr

doi:10.1055/s-0030-1260579

ACCOUNT

Synthesis of Highly Substituted Indoles via Diels-Alder/Plieninger Indolization Sequence: Applications in Total Synthesis

Katarina Sapeta, Terry P. Lebold, Michael A. Kerr*
Department of Chemistry, The University of Western Ontario, London, ON, N6A 5B7, Canada
Fax: +1(510)6613022; e-Mail: makerr@uwo.ca;

Abstract

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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

Full Text

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