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

Biosynthesis of Lipids

Biosynthesis of Lipids

Microbial membranes exhibit remarkable diversity in lipid composition, reflecting evolutionary adaptations to various environmental conditions. The three domains of life—Bacteria, Archaea, and Eukarya—synthesize membrane lipids through distinct biosynthetic pathways, leading to fundamental structural differences that impact membrane stability, function, and adaptability.Fatty Acid-Based Lipids in Bacteria and EukaryaBacteria and eukaryotes share a common fatty acid biosynthesis pathway, which...

Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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.

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

Preparation of Diols and Pinacol Rearrangement

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

You might also read

Related Articles

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

Sort by

Same author

Impact of hepatotoxicity and lipid metabolism-related toxicity on survival and quality of life in patients with high-volume metastatic hormone-sensitive prostate cancer treated with rezvilutamide in the CHART trial: a post hoc analysis.

BMC medicine·2026

Same author

Systematic Chemical Profiling of Allii macrostemonis Bulbus Based on Ultra-High-Performance Liquid Chromatography-Quadrupole-Exactive Orbitrap Mass Spectrometry.

Journal of separation science·2026

Same author

Lignans Alleviate Depression by Modulating the Gut-Brain Axis: Effect and Mechanism Based on Multi-Omics Analyses.

BioFactors (Oxford, England)·2026

Same author

A Cationic Eu-Based Metal-Organic Framework and Its Mixed Matrix Membranes for Sensitive Detection of Nitroaromatic Explosives.

Inorganic chemistry·2026

Same author

PM<sub>2.5</sub>-Bound Organophosphate Esters and Childhood Sleep Disorders: Evidence from the Pearl River Delta Study.

Toxics·2026

Same author

Corrigendum to "Angiotensin II upregulates K<sub>Ca</sub>3.1 channels and stimulates cell proliferation in rat cardiac fibroblasts". [Biochem. Pharmacol. 85 (2013) 1486-1494].

Biochemical pharmacology·2026

Search research articles

Related Experiment Video

Updated: Jun 6, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Concise total synthesis of largazole.

Qiong Xiao¹, Li-Ping Wang, Xiao-Zhen Jiao

¹Peking Union Medical College & Chinese Academy of Medical Sciences, Institute of Materia Medica, Beijing, China.

Journal of Asian Natural Products Research

|November 10, 2010

Summary

The total synthesis of largazole was achieved using a novel method. A key step involved the Nagao thiazolidinethione auxiliary for stereoselective reactions and peptide formation.

More Related Videos

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Related Experiment Videos

Last Updated: Jun 6, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

Area of Science:

Organic Chemistry
Synthetic Chemistry
Medicinal Chemistry

Background:

Largazole is a biologically active marine natural product.
The synthesis of complex molecules like largazole presents significant challenges.

Purpose of the Study:

To achieve a concise total synthesis of largazole.
To explore the utility of the Nagao thiazolidinethione auxiliary in complex molecule synthesis.

Main Methods:

The synthesis employed a Nagao thiazolidinethione auxiliary.
A diastereoselective acetate aldol reaction was a key transformation.
The auxiliary also served as an acylating agent for peptide bond formation.

Main Results:

A concise and efficient total synthesis of largazole was accomplished.
The Nagao auxiliary enabled high diastereoselectivity in the aldol reaction.
The auxiliary facilitated straightforward peptide coupling.

Conclusions:

The developed synthetic route is efficient for largazole production.
The Nagao thiazolidinethione auxiliary is a versatile tool for stereoselective synthesis and peptide coupling.