Synthesis 2019; 51(04): 787-815
DOI: 10.1055/s-0037-1611702
review
© Georg Thieme Verlag Stuttgart · New York

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

Igor V. Trushkov
a  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow, 119991, Russian Federation
,
Maxim G. Uchuskin
b  Perm State University, Bukireva 15, Perm, 614990, Russian Federation
,
Vladimir T. Abaev
c  K. L. Khetagurov North-Ossetian State University, Vatutina 43–46, Vladikavkaz, 362025, Russian Federation
,
d  Department of Chemistry and Pharmacy, Medicinal Chemistry, University of Erlangen-Nuremberg, Nikolaus-Fiebiger-Str. 10, ­Erlangen 91058, Germany   Email: olga.serdyuk@fau.de
› Author Affiliations
M.G.U. thanks the Ministry of Education and Science of the Russian Federation (Project No. 4.5371.2017/8.9) and Russian Foundation for Basic Research (grant No. 16-03-00513 А). V.T.A. thanks Russian Foundation for Basic Research (grant No. 16-03-00807 А).
Further Information

Publication History

Received: 04 October 2018

Accepted after revision: 13 November 2018

Publication Date:
24 January 2019 (eFirst)

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

 
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