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Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

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One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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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...
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Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

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Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
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Asymmetric Synthesis of Rupestonic Acid and Pechueloic Acid.

Pan Han1, Zhu Zhou1, Chang-Mei Si1

  • 1Institutes of Biomedical Sciences and School of Pharmacy, Fudan University , 220 Handan Road, Shanghai 200433, China.

Organic Letters
|December 7, 2017
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Summary

This study efficiently synthesized rupestonic acid and pechueloic acid using a convergent strategy. Key transformations included ring-closing metathesis and Wittig rearrangement, utilizing recycled chiral lactones.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Rupestonic acid and pechueloic acid are complex natural products.
  • Efficient synthetic routes are crucial for their availability.

Purpose of the Study:

  • To develop an efficient convergent synthesis of rupestonic acid (5) and pechueloic acid (3).
  • To explore the utility of recycled chiral lactones in complex molecule synthesis.

Main Methods:

  • Convergent synthesis strategy.
  • Utilized chiral lactone 13 derived from saponin glycosides.
  • Employed ring-closing metathesis (RCM), SmI2-prompted intermolecular addition, and [2,3]-Wittig rearrangement.

Main Results:

  • Successfully synthesized rupestonic acid (5) and pechueloic acid (3).
  • Demonstrated the effectiveness of RCM, SmI2-prompted addition, and [2,3]-Wittig rearrangement in subunit synthesis.
  • Prepared key chiral fragment 11 from recycled chiral lactone 13.

Conclusions:

  • The developed convergent strategy provides an efficient route to rupestonic acid and pechueloic acid.
  • Recycling chiral lactones is a viable approach for accessing key chiral fragments.
  • The employed synthetic transformations are effective for constructing complex molecular architectures.