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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.7K
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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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

13.7K
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.
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

3.0K
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).
3.0K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.1K
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.
5.1K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.9K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.9K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.2K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
3.2K

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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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First ketene cycloaddition approach to (±)-junionone.

Ihsan Erden1, Samuel E Watson1

  • 1San Francisco State University, Department of Chemistry and Biochemistry, 1600 Holloway Avenue, San Francisco, CA 94132, USA.

Tetrahedron Letters
|January 5, 2016
PubMed
Summary
This summary is machine-generated.

Researchers achieved the first total synthesis of junionone, a unique plant-derived monocyclic cyclobutane monoterpenoid. This novel synthesis uniquely utilizes a ketene cycloaddition to construct the core four-membered ring structure.

Keywords:
Huang-Minlon reductionWacker-Tsuji oxidationcyclobutanonedimethylketenejunionone

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Synthetic Methodology

Background:

  • Junionone is the first identified monocyclic cyclobutane monoterpenoid from a plant source.
  • Existing synthetic routes to junionone do not involve ketene cycloaddition for the four-membered ring construction.

Purpose of the Study:

  • To report the first total synthesis of junionone.
  • To introduce a novel synthetic strategy employing ketene cycloaddition for junionone synthesis.

Main Methods:

  • Total synthesis of junionone.
  • Utilizing ketene cycloaddition for cyclobutane ring formation.
  • Starting material: commercially available 1,5-hexadiene.

Main Results:

  • Successful total synthesis of junionone.
  • Demonstration of a novel ketene cycloaddition strategy for constructing the cyclobutane core.
  • The synthesis provides a new route to this unique monoterpenoid.

Conclusions:

  • The developed synthetic route represents the first application of ketene cycloaddition in junionone synthesis.
  • This work expands the synthetic toolbox for accessing cyclobutane-containing natural products.