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Review

The Pictet-Spengler Reaction Updates Its Habits

1
Department of Chemistry and Technology of Drugs, “Department of Excellence 2018−2022”, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy
2
Center for Life Nano [email protected], Istituto Italiano di Tecnologia, Viale Regina Elena 291, 00161 Rome, Italy
3
Department of Chemistry and Applied Biosciences, ETH-Zürich, Vladimir-Prelog Weg 4, 8093 Zürich, Switzerland
*
Authors to whom correspondence should be addressed.
Academic Editor: Ari Koskinen
Molecules 2020, 25(2), 414; https://doi.org/10.3390/molecules25020414
Received: 13 December 2019 / Revised: 5 January 2020 / Accepted: 9 January 2020 / Published: 19 January 2020
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. View Full-Text
Keywords: Pictet-Spengler; tetrahydroisoquinoline; THIQ; tetrahydro-β-carboline; THBC; alkaloid; total synthesis; natural products; cascade reaction; multicomponent reaction Pictet-Spengler; tetrahydroisoquinoline; THIQ; tetrahydro-β-carboline; THBC; alkaloid; total synthesis; natural products; cascade reaction; multicomponent reaction
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MDPI and ACS Style

Calcaterra, A.; Mangiardi, L.; Delle Monache, G.; Quaglio, D.; Balducci, S.; Berardozzi, S.; Iazzetti, A.; Franzini, R.; Botta, B.; Ghirga, F. The Pictet-Spengler Reaction Updates Its Habits. Molecules 2020, 25, 414. https://doi.org/10.3390/molecules25020414

AMA Style

Calcaterra A, Mangiardi L, Delle Monache G, Quaglio D, Balducci S, Berardozzi S, Iazzetti A, Franzini R, Botta B, Ghirga F. The Pictet-Spengler Reaction Updates Its Habits. Molecules. 2020; 25(2):414. https://doi.org/10.3390/molecules25020414

Chicago/Turabian Style

Calcaterra, Andrea, Laura Mangiardi, Giuliano Delle Monache, Deborah Quaglio, Silvia Balducci, Simone Berardozzi, Antonia Iazzetti, Roberta Franzini, Bruno Botta, and Francesca Ghirga. 2020. "The Pictet-Spengler Reaction Updates Its Habits" Molecules 25, no. 2: 414. https://doi.org/10.3390/molecules25020414

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