The Pictet-Spengler Reaction Updates Its Habits

Molecules

Francesca Ghirga¹  Simone Berardozzi²  Antonia Iazzetti³  Silvia Balducci³  Andrea Calcaterra³  Roberta Franzini³  Laura Mangiardi³  Giuliano Delle Monache³  Bruno Botta³  Deborah Quaglio³ 

[1] Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Viale Regina Elena 291, 00161 Rome, Italy;Department of Chemistry and Applied Biosciences, ETH-Zürich, Vladimir-Prelog Weg 4, 8093 Zürich, Switzerland;Department of Chemistry and Technology of Drugs, “Department of Excellence 2018−2022”, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy;

关键词: pictet-spengler;    tetrahydroisoquinoline;    thiq;    tetrahydro-β-carboline;    thbc;    alkaloid;    total synthesis;    natural products;    cascade reaction;    multicomponent reaction;   

DOI  :  10.3390/molecules25020414

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown