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

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.4K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.4K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

9.8K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
9.8K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

6.7K
The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
6.7K
Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives01:15

Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

2.9K
Nucleophilic acyl substitution is an important class of substitution reactions involving a nucleophile and an acyl compound, such as carboxylic acids and their derivatives. In these reactions, the leaving group attached to the acyl group is substituted by a nucleophile. The general mechanism proceeds via two steps.
2.9K
Phase II Reactions: Acetylation Reactions01:24

Phase II Reactions: Acetylation Reactions

161
Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...
161
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

2.8K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
2.8K

You might also read

Related Articles

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

Sort by
Same author

The Missing Link in Ferrocenophane Chemistry: Isolation of a Carba[1]Ferrocenophane.

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

Substituent-Dependent Structural Trends in Thermal Condensation of Silanetriols and Disiloxanetetraols.

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

Dual Modality and Site-differentiated Sentinel Node Mapping in Vulvar Cancer.

Anticancer research·2026
Same author

A General Strategy for the Synthesis of Jerangolids Enabled by π-allyl Stille Coupling.

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

Flash Communication: (Ph<sub>3</sub>P)<sub>2</sub>N<sub>2</sub>Aza-Wittig Reagent for Metal Carbonyls.

Organometallics·2026
Same author

Pentasilacyclopentadienide: A Hückel aromatic species at the border of resonance and equilibrium.

Science (New York, N.Y.)·2026

Related Experiment Video

Updated: May 25, 2025

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
06:00

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

7.4K

Transannular Acylation Facilitates C5-C9 Bond Formation in Hyperforin Total Synthesis.

Julien A König1, Sebastian Frey1, Bernd Morgenstern2

  • 1Organic Chemistry II, Saarland University, 66123 Saarbrücken, Germany.

Organic Letters
|February 27, 2025
PubMed
Summary

Chemists developed a novel linear total synthesis for hyperforin, a complex molecule with significant biological activity. This new method efficiently constructs the core bicyclo[3.3.1]nonane-2,4,9-trione framework.

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

7.3K
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

12.9K

Related Experiment Videos

Last Updated: May 25, 2025

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
06:00

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

7.4K
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

7.3K
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

12.9K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Hyperforin is a key compound in polycyclic polyprenylated acylphloroglucinols.
  • Its complex structure and biological activity make it a desirable synthetic target.
  • Previous synthetic routes have been explored over the last two decades.

Purpose of the Study:

  • To report an innovative linear total synthesis of hyperforin.
  • To provide an efficient method for constructing the hyperforin scaffold.

Main Methods:

  • The synthesis involves the formation of a bicyclo[3.3.1]nonane-2,4,9-trione framework.
  • Key steps include transannular acylation of an eight-membered ring.
  • Late-stage bridgehead substitution is employed.

Main Results:

  • A novel linear total synthesis of hyperforin has been achieved.
  • The synthesis successfully establishes the core trione framework.
  • The strategy allows for late-stage functionalization.

Conclusions:

  • The reported synthesis offers an efficient and innovative approach to hyperforin.
  • This method advances the synthetic chemistry of complex natural products.
  • The accessibility of hyperforin is improved for further biological investigation.