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

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

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 rearrangements are...
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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.

You might also read

Related Articles

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

Sort by
Same author

Discovery of Ligands for the TNFR1 Extracellular Domain Using Fragment-Based Drug Discovery.

ChemMedChem·2026
Same author

Structure elucidation of leadbeaterin-1, an ichthyotoxin associated with fish-killing blooms of Chrysochromulina leadbeateri in Northern Norwegian fjords.

Harmful algae·2026
Same author

Potential Adjunctive Role of Osteopathic Manipulative Medicine in the Management of Cancer-Related Bone Pain: A Narrative Review.

Cureus·2026
Same author

Polypeptides synthesized by common bacteria in the human gut improve rodent metabolism.

Nature microbiology·2025
Same author

<i>De novo</i> design of a mechano-pharmaceutical screening platform against formation of individual beta-amyloid oligomers.

Cell reports. Physical science·2025
Same author

Sine Ydun Larsen (1943-2025).

Acta crystallographica. Section A, Foundations and advances·2025

Related Experiment Video

Updated: Jun 24, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Polycyclic alkaloids via transannular Mannich reactions.

Paulo Vital1, Masood Hosseini, M Sundaram Shanmugham

  • 1Department of Chemistry, Technical University of Denmark, 201 Kemitorvet, Lyngby, DK-2800 Kgs, Denmark.

Chemical Communications (Cambridge, England)
|March 26, 2009
PubMed
Summary

Researchers synthesized a key tricyclic compound, the core structure of cylindricine and lepadiformine alkaloids. This was achieved using a novel transannular Mannich reaction on a macrocyclic diketoamine in one step.

More Related Videos

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

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Related Experiment Videos

Last Updated: Jun 24, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

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

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis

Background:

  • Cylindricine and lepadiformine alkaloids possess complex tricyclic frameworks.
  • Efficient synthetic routes to these alkaloid cores are valuable for medicinal chemistry.

Purpose of the Study:

  • To develop a novel and efficient method for synthesizing the tricyclic framework of cylindricine and lepadiformine alkaloids.
  • To demonstrate the first application of a transannular Mannich reaction in the synthesis of such macrocyclic diketoamines.

Main Methods:

  • A single-step synthesis was employed.
  • The key reaction involved a transannular Mannich reaction.
  • The substrate was a macrocyclic diketoamine.

Main Results:

  • A tricyclic compound, representing the core structure of target alkaloids, was successfully prepared.
  • The synthesis was achieved in a single operational step.
  • This represents the first reported instance of a transannular Mannich reaction involving a macrocyclic diketoamine.

Conclusions:

  • The developed synthetic strategy provides an efficient route to a key alkaloid framework.
  • Transannular Mannich reactions are a viable method for constructing complex macrocyclic systems.
  • This work facilitates further exploration of cylindricine and lepadiformine analogs.