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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

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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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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A Dipolar Cycloaddition Approach Toward the Kopsifoline Alkaloid Framework.

Xuechuan Hong1, Stefan France, Albert Padwa

  • 1Department of Chemistry, Emory University, Atlanta, GA 30322, USA.

Tetrahedron
|August 22, 2007
PubMed
Summary

This study presents a novel metal-catalyzed domino reaction for synthesizing the kopsifoline alkaloid skeleton. The method utilizes 1,3-dipolar cycloaddition and subsequent steps to construct the complex heterocyclic structure.

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Kopsifoline alkaloids are a complex family of natural products with significant biological activity.
  • Efficient synthetic routes to kopsifoline alkaloids are crucial for further biological investigation and potential drug development.

Purpose of the Study:

  • To develop a novel and efficient synthetic strategy for constructing the core heterocyclic skeleton of kopsifoline alkaloids.
  • To employ a metal-catalyzed domino reaction as the key step in the synthesis.

Main Methods:

  • A rhodium(II)-catalyzed reaction of a diazo ketoester generated a carbonyl ylide dipole.
  • The carbonyl ylide underwent a 1,3-dipolar cycloaddition with an indole pi-bond.
  • Subsequent ring opening, reductive dehydroxylation, and F-ring closure completed the skeleton.

Main Results:

  • The study successfully constructed the heterocyclic skeleton of kopsifoline alkaloids.
  • A key silyl enol ether intermediate was formed, facilitating the final F-ring closure.
  • The metal-catalyzed domino reaction proved effective for assembling the complex structure.

Conclusions:

  • A novel synthetic route to kopsifoline alkaloids has been established using a metal-catalyzed domino reaction.
  • This approach offers an efficient method for accessing the kopsifoline skeleton, valuable for natural product synthesis.
  • The developed methodology provides a foundation for synthesizing analogs and exploring their biological activities.