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

Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Sharpless Epoxidation02:57

Sharpless Epoxidation

The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...

You might also read

Related Articles

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

Sort by
Same author

Pharmaceutical Manufacturer Kickback Resolutions and Associated Financial Penalties, 2000-2025.

JAMA network open·2026
Same author

Politics, Science, and the Future of FDA Drug Regulation: FDA's Review of Mifepristone REMS as a Litmus Test.

JAMA·2026
Same author

Public sector innovation and the constraints of 'platform thinking': An account of Johnson & Johnson's adenoviral vector vaccines.

Social science & medicine (1982)·2025
Same author

Discovery of PF-07054894, a Potent Squaramide-Based CCR6 Antagonist Displaying High CXCR2 Selectivity.

Journal of medicinal chemistry·2025
Same author

Peptidylarginine Deiminase (PAD) Inhibitor Optimization through Displacement of a Trapped Water Molecule.

ACS medicinal chemistry letters·2025
Same author

Conformational Role of Methyl in the Potency of Cyclohexane-Substituted Squaramide CCR6 Antagonists.

Journal of medicinal chemistry·2025

Related Experiment Video

Updated: May 10, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-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

A dioxane template for highly selective epoxy alcohol cyclizations.

James J Mousseau1, Christopher J Morten, Timothy F Jamison

  • 1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave. Cambridge, MA, 02139, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 19, 2013
PubMed
Summary
This summary is machine-generated.

Researchers developed a new synthetic method for ladder polyether natural products, crucial for understanding harmful algal blooms (HABs) and developing anticancer drugs. This method utilizes 1,3-dioxan-5-ol substrates for highly selective epoxide cyclizations.

Keywords:
cyclizationepoxidespolyethersregioselectivitytemplate synthesis

More Related Videos

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

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

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Related Experiment Videos

Last Updated: May 10, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-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

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

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

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Chemical Biology

Background:

  • Ladder polyether natural products are complex molecules found in harmful algal blooms (HABs).
  • These compounds possess high functional-group density and numerous stereocenters, posing synthetic challenges.
  • Their toxicity impacts ecosystems and economies, but their ion channel blocking activity suggests anticancer potential.

Purpose of the Study:

  • To develop efficient synthetic routes for ladder polyether natural products.
  • To understand the biosynthesis of these compounds for HAB mitigation and analog synthesis.
  • To explore novel synthetic strategies for accessing diverse ladder polyether structures.

Main Methods:

  • Utilized 1,3-dioxan-5-ol substrates to induce 'enhanced template effects' in water-promoted epoxide cyclizations.
  • Investigated various Brønsted and Lewis acidic and basic conditions to optimize selectivity.
  • Explored alternative synthetic pathways and cascade sequences with polyepoxides.

Main Results:

  • Achieved near complete endo-to-exo selectivity in epoxide cyclizations, favoring tetrahydropyran (THP) ring formation over tetrahydrofuran (THF) rings.
  • Demonstrated the superior selectivity of the 1,3-dioxan-5-ol template compared to previous methods.
  • Showcased the versatility of the new reaction template through cascade sequences.

Conclusions:

  • The developed method provides a powerful tool for the synthesis of ladder polyether natural products.
  • This advancement aids in understanding HAB toxins and facilitates the creation of potential anticancer drug analogs.
  • The study highlights a versatile and highly selective synthetic strategy for complex natural products.