Full solid-phase total synthesis of macrocyclic natural peptides using four-dimensionally orthogonal protective groups

2019 ◽  
Vol 17 (27) ◽  
pp. 6519-6527
Author(s):  
Hiroaki Itoh ◽  
Masayuki Inoue
Keyword(s):  
Total Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Protective Group ◽  
Phase Synthesis ◽  
Protective Groups ◽  
Natural Peptides

This review focuses on four-dimensionally orthogonal protective group strategies for the full solid-phase synthesis of macrocyclic natural peptides.

Facile Solid-Phase Synthesis of Sulfated Tyrosine-Containing Peptides: Total Synthesis of Human Big Gastrin-II and Cholecystokinin (CCK)-391,2

2001 ◽  
Vol 66 (1) ◽  
pp. 1-10 ◽  
Author(s):  
Kouki Kitagawa ◽  
Chikako Aida ◽  
Hidetoshi Fujiwara ◽  
Takeshi Yagami ◽  
Shiroh Futaki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

scholarly journals The Pictet-Spengler Reaction Updates Its Habits

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 414 ◽  
Author(s):  
Andrea Calcaterra ◽  
Laura Mangiardi ◽  
Giuliano Delle Monache ◽  
Deborah Quaglio ◽  
Silvia Balducci ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Multicomponent Reaction ◽  
Michael Addition ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Synthetic Method ◽  
Ring Closing Metathesis ◽  
Phase Synthesis ◽  
Acid Catalyzed ◽  
High Yields

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.

Divergent Solid-Phase Synthesis of Natural Product-Inspired Bipartite Cyclodepsipeptides: Total Synthesis of Seragamide A

2015 ◽  
Vol 21 (14) ◽  
pp. 5311-5316 ◽  
Author(s):  
Hans-Dieter Arndt ◽  
Stefano Rizzo ◽  
Christina Nöcker ◽  
Vijay N. Wakchaure ◽  
Lech-Gustav Milroy ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

Solid-phase synthesis of coralmycin A/epi-coralmycin A and desmethoxycoralmycin A

2021 ◽  
Author(s):  
Paige Hawkins ◽  
Dennis Y. Liu ◽  
Roger Gareth Linington ◽  
Richard James Payne
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

The total synthesis of the natural product coralmycin A/epi-coralmycin A, as well as a desmethoxy analogue is described. Synthesis was achieved via a divergent, bidirectional solid-phase strategy, including a key...

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