scholarly journals Polyether Natural Product Inspired Cascade Cyclizations: Autocatalysis on π‐Acidic Aromatic Surfaces

2020 ◽  
Vol 132 (35) ◽  
pp. 15205-15209
Author(s):  
Miguel Paraja ◽  
Xiaoyu Hao ◽  
Stefan Matile
2021 ◽  
Author(s):  
K. R. Holman ◽  
A. M. Stanko ◽  
S. E. Reisman

This tutorial review highlights the use of palladium-catalyzed cascade cyclizations in natural product synthesis, focusing on cascades that construct multiple rings and form both C–C and C–X (X = O, N) bonds in a single synthetic operation.


Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 67-82 ◽  
Author(s):  
Anthony Barrett ◽  
Tsz-Kan Ma ◽  
Thomas Mies

Cascade polyene cyclization reactions are highly efficient and elegant bioinspired transformations that involve simultaneous multiple bond constructions to rapidly generate complex polycyclic molecules. This review summarizes the most prominent work on a variety of cationic and radical cascade cyclizations and their applications in natural product synthesis published between 2014 and 2018.1 Introduction2 Cationic Polyene Cyclizations2.1 Lewis Acid Mediated Polyene Cyclizations2.2 Brønsted Acid Mediated Polyene Cyclizations2.3 Halogen Electrophile Initiated Polyene Cyclizations2.4 Sulfur Electrophile Initiated Polyene Cyclizations2.5 Transition-Metal-Mediated Cationic Polyene Cyclizations3 Radical Polyene Cyclizations3.1 Transition-Metal-Mediated Radical Polyene Cyclizations3.2 Photocatalyst-Mediated Polyene Cyclizations4 Origin of Stereocontrol in Polyene Cyclizations5 Conclusion


Synthesis ◽  
2018 ◽  
Vol 50 (04) ◽  
pp. 700-710 ◽  
Author(s):  
Hiroaki Ohno ◽  
Shinsuke Inuki

Cascade reactions (also represented as domino reactions) realize the step-economical direct construction of natural product core structures. The use of atom-economical elementary reactions in cascade processes can minimize waste production and avoid prefunctionalization of the substrates. Palladium catalysis, which promotes a variety of atom-economical elementary reactions, has long been used as a powerful approach to the direct formation of complex heterocycles. In this short review, palladium-catalyzed cascade reactions for the construction of core structures of natural products reported in the last decade­ are highlighted.1 Introduction2 Reactions Terminated with Heteronucleophiles2.1 Termination with Nitrogen Nucleophiles2.2 Termination with Oxygen Nucleophiles3 Reactions Terminated with Carbon Functional Groups3.1 Termination with Carbon Nucleophiles3.2 Termination with Heck-Type Reactions4 Conclusion


Author(s):  
Ardalan A. Nabi ◽  
Lydia M. Scott ◽  
Daniel P. Furkert ◽  
Jonathan Sperry

The rare benzoxazepine ring in the alkaloid inducamide C is unstable and prone to rearrangement, indicating that structural revision of the natural product may be necessary.


Planta Medica ◽  
2008 ◽  
Vol 74 (09) ◽  
Author(s):  
V Myrianthopoulos ◽  
P Magiatis ◽  
AL Skaltsounis ◽  
L Meijer ◽  
E Mikros

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