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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.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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.
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
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Anodic coupling reactions: a sequential cyclization route to the arteannuin ring skeleton.

Honghui Wu1, Kevin D Moeller

  • 1Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.

Organic Letters
|October 4, 2007
PubMed
Summary

Researchers synthesized the arteannuin ring skeleton using two intramolecular anodic olefin coupling reactions. A N,O-ketene acetal initiating group proved more effective than an enol ether for the first cyclization, while the second coupled an endocyclic enol ether to a furan ring.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • The arteannuin ring skeleton is a core structure in several biologically active compounds.
  • Efficient synthetic routes to complex natural products are crucial for drug discovery and development.

Purpose of the Study:

  • To develop a novel synthetic strategy for constructing the arteannuin ring skeleton.
  • To explore the utility of intramolecular anodic olefin coupling reactions in complex molecule synthesis.

Main Methods:

  • Two intramolecular anodic olefin coupling reactions were employed.
  • The first reaction utilized a furan ring and investigated different initiating groups (enol ether vs. N,O-ketene acetal).
  • The second reaction involved coupling an endocyclic enol ether to the furan ring.

Main Results:

  • The use of a N,O-ketene acetal initiating group significantly improved the efficiency of the first cyclization.
  • The second electrolysis reaction successfully generated the crucial tetrasubstituted carbon center of the arteannuin ring.
  • The study demonstrated the feasibility of constructing the arteannuin core via anodic olefin coupling.

Conclusions:

  • Intramolecular anodic olefin coupling provides an effective method for assembling the arteannuin skeleton.
  • The choice of initiating group is critical for the success of these cyclization reactions.
  • This synthetic approach offers a valuable tool for accessing arteannuin derivatives and related compounds.