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[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.
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.
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).
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.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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.

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Published on: February 6, 2019

Access to a welwitindolinone core using sequential cycloadditions.

Barry M Trost1, Patrick J McDougall

  • 1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu

Organic Letters
|July 18, 2009
PubMed
Summary
This summary is machine-generated.

Researchers developed a concise synthesis for welwitindolinone alkaloids using sequential cycloaddition reactions. This novel approach efficiently constructs the core skeleton of these complex natural products.

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Synthetic Methodology

Background:

  • Welwitindolinone alkaloids are a class of complex natural products with significant biological activity.
  • Existing synthetic routes to the welwitindolinone core are often lengthy and lack efficiency.
  • Developing concise and enantioselective methods is crucial for accessing these valuable compounds.

Purpose of the Study:

  • To establish a streamlined synthetic strategy for the core skeleton of welwitindolinone alkaloids.
  • To demonstrate the utility of sequential cycloaddition reactions in natural product synthesis.
  • To provide a foundation for the total synthesis of welwitindolinone family members.

Main Methods:

  • Utilized a palladium-catalyzed enantioselective [6 + 3] trimethylenemethane cycloaddition reaction.
  • Employed a tropone derivative as the key substrate for the initial cycloaddition.
  • Performed subsequent modifications and an intramolecular [4 + 2] cycloaddition to form the oxindole core.

Main Results:

  • Successfully generated the bicyclo[4.3.1]decadiene intermediate via the [6 + 3] cycloaddition.
  • Constructed the oxindole moiety through an intramolecular [4 + 2] cycloaddition.
  • Established a concise and efficient route to the fundamental welwitindolinone skeleton.

Conclusions:

  • The developed sequential cycloaddition strategy offers a powerful and concise approach to the welwitindolinone core.
  • This methodology advances the synthesis of complex alkaloids and related natural products.
  • The findings pave the way for further exploration and derivatization of welwitindolinones.