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Preparation of Amides01:29

Preparation of Amides

3.8K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.8K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

4.3K
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...
4.3K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.5K
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.
5.5K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.2K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.2K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.2K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.2K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.5K
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.
3.5K

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The Formosalides: Structure Determination by Total Synthesis.

Saskia Schulthoff1, James Y Hamilton1, Marc Heinrich1

  • 1Max-Planck-Institut für Kohlenforschung, 45470, Mülheim/Ruhr, Germany.

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|September 18, 2020
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Total synthesis confirmed the structure of cytotoxic formosalide marine macrolides. This modular approach enabled confident assignment of their stereochemistry and facilitated access to various isomers.

Keywords:
alkyne metathesisnatural productsplatinumstructure elucidationtotal synthesis

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Area of Science:

  • Marine natural products chemistry
  • Organic synthesis
  • Medicinal chemistry

Background:

  • Formosalides are cytotoxic marine macrolides with complex structures.
  • Their exact stereochemistry and total synthesis pathways remain challenging.

Purpose of the Study:

  • To confirm the constitution of formosalides through total synthesis.
  • To assign the previously unknown stereostructure of these marine macrolides.
  • To develop a modular synthetic strategy for accessing formosalide isomers.

Main Methods:

  • Modular total synthesis utilizing catalyst-controlled stereocenter formation.
  • Late-stage macrocyclization via ring-closing alkyne metathesis.
  • Platinum-catalyzed transannular hydroalkoxylation/ketalization for polycyclic core construction.
  • Stille coupling for side chain attachment.

Main Results:

  • Successful total synthesis of formosalides, confirming their structure.
  • Confident assignment of the previously unknown stereostructure.
  • Demonstration of a flexible synthetic blueprint enabling access to isomers.
  • Establishment of key transformations for constructing the complex polycyclic framework.

Conclusions:

  • The total synthesis validates the proposed structure of formosalides.
  • The developed modular strategy provides a reliable route to formosalide analogs.
  • This work advances the understanding and accessibility of complex marine macrolides for further biological investigation.