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

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.
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
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...

You might also read

Related Articles

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

Sort by
Same author

<i>Pogostemon cablin</i> Constituents: A Promising Source of Natural Fungicides and Herbicides.

Journal of agricultural and food chemistry·2025
Same author

Transparent Poly(amide-imide)s with Low Coefficient of Thermal Expansion from Trifluoromethylated Trimellitic Anhydride.

Polymers·2025
Same author

Chemical structure-biological activity of 1,4-naphthoquinone analogs as potential Aedes aegypti larvicides.

Pest management science·2025
Same author

Synthesis, Herbicidal Activity, and Structure-Activity Relationships of O-Alkyl Analogues of Khellin and Visnagin.

Journal of agricultural and food chemistry·2023
Same author

Isolation of Two Plasticizers, Bis(2-ethylhexyl) Terephthalate and Bis(2-ethylhexyl) Phthalate, from Capparis spinosa L. Leaves.

Chemistry & biodiversity·2023
Same author

Deciphering Plant-Insect-Microorganism Signals for Sustainable Crop Production.

Biomolecules·2023

Related Experiment Video

Updated: May 15, 2026

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

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Solid phase versus solution phase synthesis of heterocyclic macrocycles.

Seong Jong Kim1, Shelli R McAlpine

  • 1School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia.

Molecules (Basel, Switzerland)
|January 18, 2013
PubMed
Summary
This summary is machine-generated.

A solid phase synthesis route for urukthapelstatin A (Ustat A) is superior to solution phase methods. This solid phase approach allows for rapid peptide generation and facile cyclization, enabling straightforward synthesis of Ustat A and its analogs.

More Related Videos

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

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
05:17

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

Published on: February 9, 2021

Related Experiment Videos

Last Updated: May 15, 2026

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

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

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

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
05:17

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

Published on: February 9, 2021

Area of Science:

  • Natural Product Synthesis
  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • Urukthapelstatin A (Ustat A) is a cytotoxic natural product with a complex structure.
  • Traditional solution phase synthesis methods can be laborious and time-consuming.

Purpose of the Study:

  • To compare solution phase and solid phase synthesis routes for Ustat A.
  • To establish an efficient and rapid method for Ustat A synthesis.
  • To explore the potential for analog synthesis.

Main Methods:

  • Solid phase peptide synthesis (SPPS) for linear precursor generation.
  • Solution phase synthesis for comparison.
  • Cyclization strategies for peptide backbone formation.
  • Oxazole ring formation within the Ustat A structure.

Main Results:

  • Solid phase synthesis proved superior to solution phase methods.
  • Rapid generation of a flexible linear peptide precursor was achieved via solid phase.
  • Facile cyclization and straightforward formation of three oxazoles were observed.
  • The solid phase route is amenable to the synthesis of Ustat A analogs.

Conclusions:

  • Solid phase synthesis offers a more efficient and rapid route to Ustat A compared to solution phase.
  • The developed solid phase method facilitates the generation of Ustat A precursors and subsequent structural modifications.
  • This approach is highly suitable for the discovery of novel Ustat A analogs.