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The Pictet-Spengler Reaction Updates Its Habits
The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) follow...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7024544/ https://www.ncbi.nlm.nih.gov/pubmed/31963860 http://dx.doi.org/10.3390/molecules25020414 |
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author | Calcaterra, Andrea Mangiardi, Laura Delle Monache, Giuliano Quaglio, Deborah Balducci, Silvia Berardozzi, Simone Iazzetti, Antonia Franzini, Roberta Botta, Bruno Ghirga, Francesca |
author_facet | Calcaterra, Andrea Mangiardi, Laura Delle Monache, Giuliano Quaglio, Deborah Balducci, Silvia Berardozzi, Simone Iazzetti, Antonia Franzini, Roberta Botta, Bruno Ghirga, Francesca |
author_sort | Calcaterra, Andrea |
collection | PubMed |
description | The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations. |
format | Online Article Text |
id | pubmed-7024544 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-70245442020-03-11 The Pictet-Spengler Reaction Updates Its Habits Calcaterra, Andrea Mangiardi, Laura Delle Monache, Giuliano Quaglio, Deborah Balducci, Silvia Berardozzi, Simone Iazzetti, Antonia Franzini, Roberta Botta, Bruno Ghirga, Francesca Molecules Review The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations. MDPI 2020-01-19 /pmc/articles/PMC7024544/ /pubmed/31963860 http://dx.doi.org/10.3390/molecules25020414 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Review Calcaterra, Andrea Mangiardi, Laura Delle Monache, Giuliano Quaglio, Deborah Balducci, Silvia Berardozzi, Simone Iazzetti, Antonia Franzini, Roberta Botta, Bruno Ghirga, Francesca The Pictet-Spengler Reaction Updates Its Habits |
title | The Pictet-Spengler Reaction Updates Its Habits |
title_full | The Pictet-Spengler Reaction Updates Its Habits |
title_fullStr | The Pictet-Spengler Reaction Updates Its Habits |
title_full_unstemmed | The Pictet-Spengler Reaction Updates Its Habits |
title_short | The Pictet-Spengler Reaction Updates Its Habits |
title_sort | pictet-spengler reaction updates its habits |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7024544/ https://www.ncbi.nlm.nih.gov/pubmed/31963860 http://dx.doi.org/10.3390/molecules25020414 |
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