Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds

Dedicated to the memory of Professor Alexander V. Butin

Abstract

Indolylvinyl ketones are valuable building blocks that can be utilized for the synthesis of numerous natural products and bioactive molecules containing an indole core motif. Herein, we describe their application for the total synthesis of some alkaloids, their analogues, and a variety of other important compounds, with an emphasis on biologically active examples.

1 Introduction

2 Functionalization of the Enone C=C Bond

2.1 Reduction

2.2 Michael Addition

2.3 Cycloaddition

3 Transformation of the Carbonyl Group

3.1 Reduction

3.2 Knoevenagel Reaction

3.3 Addition of Organometallic Compounds

3.4 Olefination

4 Reactions Involving the Enone Conjugate System С=С–С=О

4.1 Reactions with 1,2-Dinucleophiles

4.2 Reactions with Compounds Bearing an Active Methylene Group

4.3 Reactions with 1,3-Dinucleophiles

4.4 Reactions with 1,4-Dinucleophiles

5 Functionalization of the Enone Methylene Group C(O)–CH₂R

5.1 Acylation/Crotonic Condensation and Related Transformations

5.2 Enolization

6 Functionalization of the Indole Core

6.1 [4+2] Cycloaddition

6.2 [3+3] Annulation

6.3 Electrocyclic Reactions

7 Miscellaneous

8 Conclusions

Key words

indoles - ketones - total synthesis - natural products - alkaloids - bioactive compounds

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