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Related Concept Videos

Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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.
[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.
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.

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The Logic, Experimental Steps, and Potential of Heterologous Natural Product Biosynthesis Featuring the Complex Antibiotic Erythromycin A Produced Through E. coli
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Recent ring distortion reactions for diversifying complex natural products.

Yu Li1, Shihao Cheng1, Yun Tian1

  • 1School of Pharmacy, Nantong University, Nantong 226001, China. zhaoyu@ntu.edu.cn.

Natural Product Reports
|August 16, 2022
PubMed
Summary

Ring distortion reactions chemically modify natural products, creating diverse, complex molecules for drug discovery. This review covers methods like ring expansion and contraction for generating novel compound libraries.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Drug Discovery

Background:

  • Chemical diversification of natural products is crucial for drug discovery.
  • Ring distortion reactions offer a unique approach to alter core molecular structures.
  • Generating structurally complex and diverse compounds is essential for high-throughput screening.

Purpose of the Study:

  • To review recent ring distortion reactions for natural product diversification.
  • To highlight complexity-to-diversity (CtD) and pseudo-natural product (pseudo-NP) strategies.
  • To assess challenges and future directions in this field.

Main Methods:

  • Review of literature on ring distortion reactions (2013-2022).
  • Categorization of reactions: ring expansion, cleavage, edge-fusion, spiro-fusion, rearrangement, and contraction.
  • Analysis of strategies like CtD and pseudo-NPs.

Main Results:

  • Ring distortion reactions effectively alter natural product core structures.
  • These reactions generate diverse, complex, natural product-like molecules.
  • The reviewed methods facilitate access to novel compound collections.

Conclusions:

  • Ring distortion reactions are powerful tools for natural product diversification.
  • This approach yields compounds suitable for various biological and medicinal applications.
  • Future research should focus on overcoming current limitations and expanding reaction scope.