Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Drug Metabolism: Phase II Reactions

Drug Metabolism: Phase II Reactions

Phase II reactions are essential for the detoxification and elimination of drugs from the body. These reactions involve the conjugation of parent drugs or their phase I metabolites with endogenous molecules, resulting in more hydrophilic drug conjugates. The primary conjugation reactions in this phase are sulfation and glucuronidation. Both sulfation and glucuronidation typically produce biologically inactive metabolites. However, in some cases involving prodrugs, active metabolites may be...

Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

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.

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme activation, sulfur...

α-Halogenation of Carboxylic Acid Derivatives: Overview

α-Halogenation of Carboxylic Acid Derivatives: Overview

Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the electrophilic halogen to produce...

Carboxylic Acid Derivatives: Overview

Carboxylic Acid Derivatives: Overview

Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:

You might also read

Related Articles

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

Sort by

Same author

Helical Topologies via [4 + 2] Cycloaddition Reactions between Structurally Complex Benzynes and Several Alkenyl Polycyclic Aromatic Compounds.

Organic letters·2026

Same author

Resolution Enhancement in 1D NMR Spectroscopy: A Guide to Using This Underappreciated Tactic.

The Journal of organic chemistry·2026

Same author

1<i>H</i>-Isoindolynes: Arynes Accessible by a One-Pot, Ambient Temperature, Three-Component Cascade.

The Journal of organic chemistry·2026

Same author

cGAS-STING pathway in lung cancer and emerging therapeutic approaches.

Drug discovery today·2026

Same author

Exploring and Comparing Existing Natural Product Databases Towards Whole Person Health Research.

AMIA ... Annual Symposium proceedings. AMIA Symposium·2026

Same author

Metastable Intermediates (Isoindenes, Isofluorenes, and Isobenzofurans) from Alkyne Precursors via Free Carbenes.

Organic letters·2026

Search research articles

Related Experiment Video

Updated: Jun 5, 2026

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

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

Published on: August 16, 2018

Access to functionalized steroid side chains via modified Julia olefination.

Enver Cagri Izgu¹, Aaron C Burns, Thomas R Hoye

¹Department of Chemistry, 207 Pleasant Street, SE, University of Minnesota, Minneapolis, Minnesota 55455, USA.

Organic Letters

|January 20, 2011

Summary

A modified Julia olefination strategy efficiently synthesized steroidal side chains. Benzothiazolyl-sulfone anions provided superior results for coupling steroidal compounds compared to phenyltetrazolyl-sulfone anions.

More Related Videos

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Related Experiment Videos

Last Updated: Jun 5, 2026

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

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

Published on: August 16, 2018

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Steroidal side chains are crucial components in many biologically active molecules.
Efficient synthesis of functionalized steroidal side chains remains a key challenge in organic chemistry.

Purpose of the Study:

To develop a modified Julia olefination strategy for accessing diverse functionalized steroidal side chains.
To compare the efficacy of different sulfone anions in coupling sterically hindered reaction partners.

Main Methods:

Utilized a modified Julia olefination employing a common sulfone donor and α-branched aldehyde acceptors.
Investigated the use of benzothiazolyl (BT)-sulfone and phenyltetrazolyl (PT)-sulfone anions for the olefination reaction.

Main Results:

Successfully synthesized various functionalized steroidal side chains.
The benzothiazolyl (BT)-sulfone anion demonstrated superior outcomes in coupling hindered steroidal substrates compared to the phenyltetrazolyl (PT)-sulfone anion, contrary to typical trends.

Conclusions:

The modified Julia olefination provides a convenient route to functionalized steroidal side chains.
The choice of sulfone anion significantly impacts the success of olefination with sterically demanding substrates, with BT-sulfone being the preferred reagent.