The Pictet-Spengler Reaction Updates Its Habits.
- Calcaterra A Department of Chemistry and Technology of Drugs, "Department of Excellence 2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
- Mangiardi L Department of Chemistry and Technology of Drugs, "Department of Excellence 2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
- Delle Monache G Department of Chemistry and Technology of Drugs, "Department of Excellence 2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
- Quaglio D Department of Chemistry and Technology of Drugs, "Department of Excellence 2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
- Balducci S Department of Chemistry and Technology of Drugs, "Department of Excellence 2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
- Berardozzi S Department of Chemistry and Applied Biosciences, ETH-Zürich, Vladimir-Prelog Weg 4, 8093 Zürich, Switzerland.
- Iazzetti A Department of Chemistry and Technology of Drugs, "Department of Excellence 2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
- Franzini R Department of Chemistry and Technology of Drugs, "Department of Excellence 2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
- Botta B Department of Chemistry and Technology of Drugs, "Department of Excellence 2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
- Ghirga F Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Viale Regina Elena 291, 00161 Rome, Italy.
- 2020-01-23
Published in:
- Molecules (Basel, Switzerland). - 2020
Pictet-Spengler
THBC
THIQ
alkaloid
cascade reaction
multicomponent reaction
natural products
tetrahydro-β-carboline
tetrahydroisoquinoline
total synthesis
Alkaloids
Biological Products
Cyclization
Models, Molecular
Ruthenium
English
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.
- Language
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- English
- Open access status
- gold
- Identifiers
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- DOI 10.3390/molecules25020414
- PMID 31963860
- Persistent URL
- https://sonar.rero.ch/global/documents/159350
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