The Pictet-Spengler Reaction Updates Its Habits

Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga

doi:10.3390/molecules25020414

Molecules (Jan 2020)

The Pictet-Spengler Reaction Updates Its Habits

Andrea Calcaterra,
Laura Mangiardi,
Giuliano Delle Monache,
Deborah Quaglio,
Silvia Balducci,
Simone Berardozzi,
Antonia Iazzetti,
Roberta Franzini,
Bruno Botta,
Francesca Ghirga

Affiliations

Andrea Calcaterra: Department of Chemistry and Technology of Drugs, “Department of Excellence 2018−2022”, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy
Laura Mangiardi: Department of Chemistry and Technology of Drugs, “Department of Excellence 2018−2022”, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy
Giuliano Delle Monache: Department of Chemistry and Technology of Drugs, “Department of Excellence 2018−2022”, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy
Deborah Quaglio: Department of Chemistry and Technology of Drugs, “Department of Excellence 2018−2022”, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy
Silvia Balducci: Department of Chemistry and Technology of Drugs, “Department of Excellence 2018−2022”, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy
Simone Berardozzi: Department of Chemistry and Applied Biosciences, ETH-Zürich, Vladimir-Prelog Weg 4, 8093 Zürich, Switzerland
Antonia Iazzetti: Department of Chemistry and Technology of Drugs, “Department of Excellence 2018−2022”, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy
Roberta Franzini: Department of Chemistry and Technology of Drugs, “Department of Excellence 2018−2022”, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy
Bruno Botta: Department of Chemistry and Technology of Drugs, “Department of Excellence 2018−2022”, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy
Francesca Ghirga: Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Viale Regina Elena 291, 00161 Rome, Italy

DOI: https://doi.org/10.3390/molecules25020414
Journal volume & issue: Vol. 25, no. 2
p. 414

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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