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Related Concept Videos

Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

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Related Experiment Video

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Green Synthesis of Quinoline-Based Ionic Liquid
05:59

Green Synthesis of Quinoline-Based Ionic Liquid

Published on: September 27, 2024

Total synthesis of (+)-chloriolide.

Timm T Haug1, Stefan F Kirsch

  • 1Department Chemie, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany.

Organic & Biomolecular Chemistry
|February 19, 2010
PubMed
Summary

Researchers achieved the first total synthesis of (+)-chloriolide, a macrolide from the fungus Chloridium virescens. This complex molecule was synthesized in 20 steps, yielding 7% overall.

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Mycology

Background:

  • (+)-Chloriolide is a 12-membered macrolide isolated from Chloridium virescens (var. chlamydosporum).
  • Macrolides are a significant class of natural products with diverse biological activities.
  • The structural complexity of (+)-chloriolide presents a synthetic challenge.

Purpose of the Study:

  • To achieve the first total synthesis of (+)-chloriolide.
  • To develop a viable synthetic route for this complex macrolide.
  • To confirm the proposed structure of (+)-chloriolide through synthesis.

Main Methods:

  • Total synthesis utilizing a longest linear sequence.
  • Employing commercially available starting materials.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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  • Multi-step organic reactions including cyclization and functional group manipulations.

    • Main Results:

    • Successful completion of the first total synthesis of (+)-chloriolide.
    • The synthesis was achieved in a 20-step longest linear sequence.
    • An overall yield of 7% was obtained from commercial materials.

    Conclusions:

    • The feasibility of synthesizing (+)-chloriolide has been demonstrated.
    • The synthetic route provides a foundation for further exploration of related macrolides.
    • This synthesis validates the structural assignment of (+)-chloriolide.