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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
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.
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.8K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.1K
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.
10.1K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.1K
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).
2.1K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.5K
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.
3.5K

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Dipolar Cycloaddition Approach toward Harmicine-Type Alkaloids: Synthesis and Stereochemical Determination.

Zuming Lin1, Luyao Wu1, Shengchao Yang1

  • 1School of Environmental and Chemical Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, People's Republic of China.

Organic Letters
|May 31, 2025
PubMed
Summary

Researchers rapidly synthesized harmicine using cycloaddition and ring reconstruction. This study also developed methods for optically enriched harmicine and harmicinic acid, aiding future medicinal chemistry research.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Harmicine and its derivatives are valuable in medicinal chemistry.
  • Efficient synthetic routes are crucial for accessing these compounds.

Purpose of the Study:

  • To develop a rapid synthesis of harmicine.
  • To establish methods for obtaining optically enriched harmicine and harmicinic acid.
  • To enable stereochemical determination of harmicinic acid derivatives.

Main Methods:

  • 1,3-dipolar cycloaddition and ring reconstruction for harmicine synthesis.
  • Enzymatic kinetic resolution for optically enriched tetrahydro-β-carboline.
  • Diastereomeric synthesis and chemical resolution for harmicinic acid.
  • Electronic circular dichroism (ECD) calculations for stereochemical determination.

Main Results:

  • A rapid and efficient synthesis of harmicine was achieved.
  • Optically enriched harmicine was successfully prepared.
  • Diastereomeric synthesis of harmicinic acid was accomplished.
  • First-time stereochemical determination of harmicinic acid derivatives was enabled.

Conclusions:

  • The developed synthetic strategies provide access to harmicine and its derivatives.
  • This work offers a platform for exploring new medicinal compounds.
  • Stereochemical insights are crucial for drug development.