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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.

Esters to β-Ketoesters: Claisen Condensation Mechanism

Esters to β-Ketoesters: Claisen Condensation Mechanism

Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the intermediate restores...

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

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

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.’

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.

β-Dicarbonyl Compounds via Crossed Claisen Condensations

β-Dicarbonyl Compounds via Crossed Claisen Condensations

Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.

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Related Experiment Video

Updated: May 26, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Cerinolactone, a hydroxy-lactone derivative from Trichoderma cerinum.

Francesco Vinale¹, Isabel Arjona Girona, Marco Nigro

¹CNR-Istituto per la Protezione delle Piante (IPP-CNR), 80055 Portici, 80055 Naples, Italy. frvinale@unina.it

Journal of Natural Products

|December 27, 2011

Summary

A new compound, cerinolactone, was isolated from Trichoderma cerinum. This novel metabolite shows antifungal activity against key plant pathogens like Pythium ultimum and Botrytis cinerea.

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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

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Last Updated: May 26, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

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

Area of Science:

Natural Product Chemistry
Mycology
Plant Pathology

Background:

Fungal metabolites are a source of novel bioactive compounds.
Trichoderma species are known producers of secondary metabolites with biological activity.
Plant diseases caused by Pythium ultimum, Rhizoctonia solani, and Botrytis cinerea result in significant agricultural losses.

Purpose of the Study:

To isolate and characterize novel metabolites from Trichoderma cerinum.
To evaluate the antifungal potential of isolated compounds against significant plant pathogens.

Main Methods:

Isolation of metabolites from fungal culture filtrates using chromatographic techniques.
Structure elucidation of the novel compound using UV, Mass Spectrometry (MS), and Nuclear Magnetic Resonance (NMR) spectroscopy (1D and 2D).
In vitro antifungal assays against Pythium ultimum, Rhizoctonia solani, and Botrytis cinerea.

Main Results:

A novel metabolite, cerinolactone (1), was isolated and structurally characterized.
Three known butenolides (harzianolide (2), T39butenolide (3), and dehydroharzianolide (4)) were co-isolated.
Cerinolactone (1) demonstrated in vitro antifungal activity against Pythium ultimum, Rhizoctonia solani, and Botrytis cinerea.

Conclusions:

Trichoderma cerinum produces a novel antifungal metabolite, cerinolactone.
Cerinolactone represents a potential lead compound for the development of new antifungal agents in agriculture.
Further research into the mechanism of action and field efficacy of cerinolactone is warranted.