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

Igor V. Trushkov; Maxim G. Uchuskin; Vladimir T. Abaev; Olga V. Serdyuk

doi:10.1055/s-0037-1611702

Synthesis, Table of Contents

Synthesis 2019; 51(04): 787-815
DOI: 10.1055/s-0037-1611702

review

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

Authors

Igor V. Trushkov

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow, 119991, Russian Federation
Maxim G. Uchuskin

^bPerm State University, Bukireva 15, Perm, 614990, Russian Federation
Vladimir T. Abaev

^cK. L. Khetagurov North-Ossetian State University, Vatutina 43–46, Vladikavkaz, 362025, Russian Federation
Olga V. Serdyuk *

^dDepartment of Chemistry and Pharmacy, Medicinal Chemistry, University of Erlangen-Nuremberg, Nikolaus-Fiebiger-Str. 10, Erlangen 91058, Germany Email: olga.serdyuk@fau.de

Abstract

All articles of this category

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

Full Text

References

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