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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

5.3K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.3K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.9K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

9.6K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
9.6K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.5K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.5K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.1K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
4.1K

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Related Experiment Video

Updated: Jan 6, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Bio-Based Approaches for Selective Cyclization.

Eléonore Moore1, Amy E Fraley2

  • 1Department of Chemistry and Applied Biosciences, ETH Zürich, Zürich, CH-8050. eleonore.moore@pharma.ethz.ch.

Chimia
|November 29, 2025
PubMed
Summary

Enzymes catalyze the creation of unique cyclic natural products for pharmaceuticals. This review covers these natural catalysts, their therapeutic compounds, and engineering efforts for medicine, focusing on terpene and Pictet-Spengler cyclization.

Keywords:
BiocatalysisBiosynthesisCyclizationNatural products

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Area of Science:

  • Biochemistry and Medicinal Chemistry
  • Natural Product Synthesis

Background:

  • Cyclic natural products are vital scaffolds in pharmaceuticals.
  • Enzymes are key catalysts for producing these complex molecules with high selectivity.
  • Natural product biosynthesis pathways offer diverse chemical structures.

Purpose of the Study:

  • To review enzymes involved in cyclic natural product biosynthesis.
  • To highlight therapeutic compounds derived from these natural products.
  • To discuss enzyme engineering for pharmaceutical applications.

Main Methods:

  • Literature review of enzymatic cyclization reactions.
  • Focus on biochemical methodologies for enzyme discovery and engineering.
  • Emphasis on terpene cyclization and Pictet-Spengler reactions.

Main Results:

  • Overview of naturally occurring cyclic compounds and their enzymatic production.
  • Discussion of engineered enzymes for tailored therapeutic compound synthesis.
  • Highlighting specific examples of enzyme-catalyzed cyclizations.

Conclusions:

  • Enzymatic cyclization is a powerful strategy for generating novel pharmaceutical scaffolds.
  • Enzyme engineering holds significant potential for developing new medicines.
  • Further research into natural catalysts can unlock new therapeutic avenues.