Recent Advances for the C–C and C–N Bond Formation in the Synthesis­ of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine­, and β-Carboline Alkaloids

Carlos E. Puerto Galvis; Vladimir V. Kouznetsov

doi:10.1055/s-0036-1589512

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(20): 4535-4561
DOI: 10.1055/s-0036-1589512

review

Recent Advances for the C–C and C–N Bond Formation in the Synthesis of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine, and β-Carboline Alkaloids

Authors

Carlos E. Puerto Galvis

Laboratorio de Química Orgánica y Biomolecular, Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta 681011, Colombia eMail: kouznet@uis.edu.co eMail: vkuznechnik@gmail.com
Vladimir V. Kouznetsov *

Laboratorio de Química Orgánica y Biomolecular, Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta 681011, Colombia eMail: kouznet@uis.edu.co eMail: vkuznechnik@gmail.com

Abstract

Alle Artikel dieser Rubrik

Abstract

Among the existing methods for the synthesis of bioactive and/or complex small molecules, organic transformations such as C–C and C–N bond formation have been significantly developed and exploited for the synthesis of diverse synthetic and natural fused aza-polycycles. The abundance and biological and physical activities of 1-phenethyl-tetrahydroisoquinolines, aporphines, homoaporphines, and β-carbolines have inspired many organic chemists to seek sustainable and efficient protocols for their preparation. However, these methodologies involve multiple steps and in most cases the key reaction step is based on the formation of new C–C and/or C–N bonds, and this is usually the critical step that lowers the yields and selectivity. This review is focused on the advances made in recent years regarding the synthesis of these selected natural fused aza-polycycles, overviewing the substrate scope, limitations, regioselectivity, and chemoselectivity, as well as related control strategies of these reactions, concentrating on developments from 2010 to 2016.

1 Introduction

2 1-Phenethyl-tetrahydroisoquinolines; Dysoxylum Alkaloids

3 Aporphines, Homoaporphines, and Semisynthetic Derivatives

4 Harmala and Eudistomin Alkaloids and Their Biological Properties

5 Metal-Catalyzed C–C Bond Formation

6 Pd-Catalyzed C–C and C–N Bond Formation

7 Metal-Catalyzed C–N Bond Formation

8 [4+2] Cycloaddition in the Synthesis Of Aporphines

9 Tandem C–N/C–C Bond Formation: The Pictet–Spengler Reaction

10 Miscellaneous Methods

11 Conclusions

Key words

tetrahydroisoquinolines - aporphines - homoaporphines - carbolines - C–C bond formation - C–N bond formation

Volltext

Referenzen

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Canthin-6-one. Isolation:

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Synthesis:

69d Soriano-Agatón F. Lagoutte D. Poupon E. Roblot F. Fournet A. Gantier JC. Hocquemiller R. J. Nat. Prod. 2005; 68: 1581
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Biological properties:

69i Kim HM. Kim SJ. Kim HY. Ryu B. Kwak H. Hur J. Choi JH. Jang DS. Bioorg. Med. Chem. Lett. 2015; 25: 1017
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Reviews:

69l Showalter HD. H. J. Nat. Prod. 2013; 76: 455
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Biological properties:

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70g See also ref. 70b

Harmicine, Isolation:

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Synthesis:

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Reviews:

71k Chakraborty I. Jana S. Synthesis 2013; 45: 3325
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(+)-Peganumine A. Isolation:

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Synthesis:

72b Carreira EM. Brandstätter M. Synfacts 2016; 12: 1113
72c Piemontesi C. Wang Q. Zhu J. J. Am. Chem. Soc. 2016; 138: 11148

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Recent Advances for the C–C and C–N Bond Formation in the Synthesis­ of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine­, and β-Carboline Alkaloids

Authors

Recent Advances for the C–C and C–N Bond Formation in the Synthesis of 1-Phenethyl-tetrahydroisoquinoline, Aporphine, Homoaporphine, and β-Carboline Alkaloids