Petasis Sequence Reactions for the Scaffold-Diverse Synthesis of Bioactive Polycyclic Small Molecules
Amrutha K Avathan Veettil1,2,3, Jan-Lukas Kirchhoff3, Lukas Brieger3
1Chemical Genomics Centre, Max Planck Institute of Molecular Physiology, Dortmund 44227, Germany.
Abstract:
The multicomponent Petasis reaction is a versatile method to access functionalized amines. The combination of Petasis reaction with subsequent ring-closing reactions is a powerful strategy to build novel polycyclic scaffolds. In this study, we report the generation of a diverse set of small molecules with polycyclic scaffolds featuring a high content of sp3-hybridized carbon atoms and multiple stereogenic centers by employing three-component Petasis reaction (3C-PR)-Intramolecular Diels-Alder (IMDA) and 3C-PR-ring-closing metathesis (RCM)-IMDA sequence reactions. This work demonstrates the wide substrate tolerance and broad applicability to access unexplored polycyclic scaffolds of biological interest using Petasis sequence reactions.
Related Concept Videos
Cycloaddition Reactions: Overview
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
ATP and Macromolecule Synthesis
Most macromolecules are composed of single subunits, or building blocks, called monomers. The monomers combine with each other using covalent bonds to form larger molecules known as polymers.
Conversion of...
Ziegler–Natta Chain-Growth Polymerization: Overview


