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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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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Pericyclic Reactions: Introduction01:17

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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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.
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Ziegler–Natta Chain-Growth Polymerization: Overview01:17

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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
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Step-Growth Polymerization: Overview01:03

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Step-growth or condensation polymerization is a stepwise reaction of bi or multifunctional monomers to form long-chain polymers. As all the monomers are reactive, most of the monomers are consumed at the early stages of the reaction to form small chains of reactive oligomers, which then combine to form long polymer chains in the late stages. Hence, the reaction has to proceed for a long time to achieve high molecular weight polymers.
Many natural and synthetic polymers are produced by...
4.7K
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.
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Updated: Mar 26, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Cascade polycyclizations in natural product synthesis.

R Ardkhean1, D F J Caputo1, S M Morrow1

  • 1Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, UK. edward.anderson@chem.ox.ac.uk.

Chemical Society Reviews
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Summary

Cascade reactions efficiently build complex molecules, especially for natural product synthesis. This review highlights recent advances in various cascade polycyclization strategies for creating intricate molecular architectures.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Natural Product Synthesis

Background:

  • Cascade (domino) reactions enable the rapid construction of molecular complexity from simple precursors.
  • These reactions are highly valuable for forging multiple rings in a single synthetic operation.
  • Natural product synthesis often requires efficient methods for building complex polycyclic structures.

Purpose of the Study:

  • To provide a tutorial review of recent advancements in cascade polycyclizations.
  • To showcase the application of these reactions in the synthesis of natural products.
  • To cover a diverse range of cascade reaction mechanisms.

Main Methods:

  • Review of recent literature on cascade polycyclizations.
  • Categorization of cascade reactions by mechanism: pericyclic, heteroatom-mediated, cationic, metal-catalyzed, organocatalytic, and radical sequences.
  • Focus on examples within natural product synthesis.

Main Results:

  • Highlights recent successful applications of various cascade polycyclization strategies.
  • Demonstrates the power of cascade reactions in efficiently assembling complex polycyclic natural products.
  • Illustrates the versatility of different catalytic and non-catalytic cascade approaches.

Conclusions:

  • Cascade polycyclizations are powerful tools for efficient natural product synthesis.
  • A wide array of mechanistic strategies exist for cascade polycyclizations.
  • Continued development in cascade reactions promises further advances in synthetic chemistry.