Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.7K
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.
2.7K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.7K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.7K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.3K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.3K
Mass Spectrometry: Cycloalkene Fragmentation00:54

Mass Spectrometry: Cycloalkene Fragmentation

1.1K
The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction.
1.1K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.9K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.9K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.6K
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.
3.6K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

π-Extended Salphen Scaffolds Enable CO<sub>2</sub> Electroreduction and Singlet Oxygen Generation.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Dual Activation of H<sub>2</sub> and CO<sub>2</sub> by a Pincer-Type Ni-Zn Heterobimetallic Complex.

Angewandte Chemie (International ed. in English)·2026
Same author

White-light powered autonomous molecular ratchet drives Pd<sup>II</sup> capsules out of equilibrium.

Chemical science·2026
Same author

Alkyne Cyclizations through Vinyl Cations and Stereoselective Allene Formation by Terpene Synthases.

Journal of the American Chemical Society·2026
Same author

Synthesis, Structure, and Thin Film Optical Properties of a Chiral Benzothiazole-Derived Squaraine.

Chemphyschem : a European journal of chemical physics and physical chemistry·2026
Same author

Systematic Discovery of Bacterial Diterpene Synthases and Structure-Guided Functional Interconversion of ShHS and CbCS.

Journal of the American Chemical Society·2026

Related Experiment Video

Updated: Jul 28, 2025

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.3K

Fragmentation and [4 + 3] cycloaddition in sodorifen biosynthesis.

Houchao Xu1, Lukas Lauterbach1, Bernd Goldfuss2

  • 1Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Bonn, Germany.

Nature Chemistry
|May 29, 2023
PubMed
Summary

Researchers elucidated the complex biosynthesis of sodorifen, a methylated sesquiterpene. The study reveals novel methyl group formation via methyltransferase-mediated cyclization and ring contraction, solving a key mechanistic puzzle.

More Related Videos

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.9K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.0K

Related Experiment Videos

Last Updated: Jul 28, 2025

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.3K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.9K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.0K

Area of Science:

  • Natural Product Biosynthesis
  • Enzymology
  • Organic Chemistry

Background:

  • Terpenes are the largest class of natural products, synthesized by terpene cyclases (TCs).
  • TCs convert acyclic precursors into complex cyclic structures via cationic intermediates.
  • The biosynthesis of highly methylated terpenes presents unique mechanistic challenges.

Purpose of the Study:

  • To resolve the intricate cyclization mechanism of sodorifen, a methylated sesquiterpene.
  • To elucidate the formation of unusual methyl groups from chain methylene carbons during sodorifen biosynthesis.
  • To investigate the roles of methyltransferases and terpene cyclases in this process.

Main Methods:

  • Isotopic-labeling experiments to trace atom movements.
  • Computational studies to model reaction pathways.
  • Biochemical analysis of enzymatic transformations.

Main Results:

  • The sodorifen cyclization mechanism was elucidated, involving methyltransferase-mediated cyclization and ring contraction with carbon extrusion.
  • An unprecedented mechanism for forming methyl groups from methylene carbons was identified.
  • A subsequent terpene cyclase-catalyzed fragmentation, hydrogen transfer, and [4+3] cycloaddition were detailed.

Conclusions:

  • The study solves the mechanistic puzzle of extra methyl group formation in sodorifen biosynthesis.
  • This work reveals novel enzymatic strategies in terpene natural product synthesis.
  • The findings contribute to understanding the diversity and evolution of terpene cyclases.