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

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.0K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.0K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.1K
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.
10.1K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

2.6K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
2.6K
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
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

8.8K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
8.8K

You might also read

Related Articles

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

Sort by
Same author

Synthesis of N-BOH Benzazaborines via a Modular GBB-Based Strategy.

Organic letters·2026
Same author

Multicomponent Reactions Involving Carbon Dioxide (CO<sub>2</sub>) and Isocyanides.

Chemical record (New York, N.Y.)·2026
Same author

Lactam enables remote boronate rearrangements to C═N bonds.

Communications chemistry·2026
Same author

Site-Divergent C-H Bond Functionalization of Free Phenols Enables Hydroxyflavanones.

The Journal of organic chemistry·2025
Same author

The Ugi Multicomponent Reaction for the One-Step Construction of Macrocycles.

Chemical record (New York, N.Y.)·2025
Same author

IMPA1-derived inositol maintains stemness in castration-resistant prostate cancer via IMPDH2 activation.

The Journal of experimental medicine·2024

Related Experiment Video

Updated: Jun 26, 2025

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

6.9K

Skeletal Editing: Ring Insertion for Direct Access to Heterocycles.

Xue Li1, Zhigang Xu1

  • 1College of Pharmacy, National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, IATTI, Chongqing University of Arts and Sciences, Chongqing 402160, China.

Molecules (Basel, Switzerland)
|May 11, 2024
PubMed
Summary

Skeleton editing, a synthetic method, streamlines drug synthesis by creating novel ring structures. This review focuses on ring insertion reactions that cleave and reform rings, advancing synthetic chemistry.

Keywords:
heterocyclesring expansionring insertionring skeletonsskeleton editing

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

6.8K
Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
05:17

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

Published on: February 9, 2021

1.5K

Related Experiment Videos

Last Updated: Jun 26, 2025

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

6.9K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.8K
Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
05:17

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

Published on: February 9, 2021

1.5K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Skeleton editing is a rapidly advancing synthetic methodology.
  • It has gained widespread acceptance in drug synthesis and development.
  • Diverse ring reactions are key to generating novel ring skeletons.

Purpose of the Study:

  • To compile and systematize reactions involving cleavage and reformation of rings.
  • To emphasize two primary reaction types in skeleton editing.
  • To explore complexities and challenges in these reactions.

Main Methods:

  • Systematic review of literature on skeleton editing reactions.
  • Focus on reactions involving cleavage of two rings followed by ring insertion.
  • Analysis of two primary types of ring insertion reactions.

Main Results:

  • Identification and categorization of key skeleton editing reactions.
  • Detailed exploration of reaction mechanisms and scope.
  • Discussion of challenges and limitations in current methodologies.

Conclusions:

  • Ring insertion reactions are pivotal for constructing novel ring skeletons.
  • Comprehensive strategies are provided to advance skeleton editing research.
  • This review aims to stimulate further research and innovation in synthetic chemistry.