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Related Concept Videos

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
[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.
Synthesis and Decomposition Reactions02:17

Synthesis and Decomposition Reactions

Synthesis and decomposition are two types of redox reactions. Synthesis means to make something, whereas decomposition means to break something. The reactions are accompanied by chemical and energy changes.
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.
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...
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).

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Related Experiment Video

Updated: May 15, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

[Synthesis of indole compounds using multifunctional synthons].

Takumi Abe1

  • 1Faculty of Pharmaceutical Sciences, Health Science University of Hokkaido, Japan. abe-t@hoku-iryo-u.ac.jp

Yakugaku Zasshi : Journal of the Pharmaceutical Society of Japan
|January 8, 2013
PubMed
Summary
This summary is machine-generated.

This review details a new method for synthesizing indole compounds using versatile building blocks called trienes and gramines. These synthons enable the efficient total synthesis of numerous complex indole alkaloids, showcasing a significant advancement in organic chemistry.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

Published on: May 27, 2015

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities

Published on: May 27, 2015

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Indole compounds and alkaloids are crucial in medicinal chemistry.
  • Efficient synthesis of complex indole alkaloids remains a challenge.

Purpose of the Study:

  • To describe a novel synthesis of indole compounds using multifunctional synthons.
  • To apply these synthons to the total synthesis of various indole alkaloids.

Main Methods:

  • Palladium-catalyzed tandem cyclization/cross-coupling for triene synthesis.
  • Indolylcuprate reaction with iminium chloride for gramine synthesis.
  • Copper(I)-catalyzed 6π-electrocyclization of hexatrienes.

Main Results:

  • Successful synthesis of key multifunctional synthons: trienes and gramines.
  • Total synthesis of ellipticine, 9-methoxyellipticine, 9-hydroxyellipticine, tetrahydroellipticine, μ-alkaloid B, μ-alkaloid D, calothrixin A, calothrixin B, tubifoline, and yuehchukene.
  • Development of an unprecedented Cu(I)-catalyzed 6π-electrocyclization reaction.

Conclusions:

  • Multifunctional synthons provide an efficient route to diverse indole alkaloids.
  • The developed synthetic strategies offer new possibilities for accessing complex natural products.
  • The novel electrocyclization reaction expands the synthetic toolkit for indole chemistry.