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Related Concept Videos

Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
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.
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
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...
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...

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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

Published on: October 4, 2019

Natural disesquiterpenoids.

Zha-Jun Zhan1, You-Min Ying, Lie-Feng Ma

  • 1College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, PR China. tianranyaowu@zjut.edu.cn

Natural Product Reports
|January 20, 2011
PubMed
Summary
This summary is machine-generated.

This review details natural dimeric sesquiterpenoids, covering their isolation, structure, biological activities, and synthesis. It also explores their biogenesis and includes syntheses that revised structures.

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Area of Science:

  • Natural Product Chemistry
  • Organic Chemistry
  • Biochemistry

Background:

  • Dimeric sesquiterpenoids are complex natural products with diverse biological activities.
  • Understanding their isolation, structure, and synthesis is crucial for drug discovery and chemical biology.

Purpose of the Study:

  • To provide a comprehensive review of natural dimeric sesquiterpenoids.
  • To discuss their isolation, structural determination, biological activities, and biomimetic synthesis.
  • To explore the biogenesis of these metabolites and present syntheses that led to structural revisions.

Main Methods:

  • Literature review of published research on dimeric sesquiterpenoids.
  • Analysis of isolation and structural determination techniques.
  • Examination of reported biological activities and synthetic strategies.
  • Discussion of biogenetic pathways and structure-activity relationships.

Main Results:

  • Compilation of known natural dimeric sesquiterpenoids.
  • Detailed account of their structural features and biological properties.
  • Overview of biomimetic synthetic approaches and their successes.
  • Inclusion of synthetic studies that resulted in structural re-assignments.
  • Extensive citation of 368 references.

Conclusions:

  • Dimeric sesquiterpenoids represent a significant class of natural products with complex structures and varied bioactivities.
  • Biomimetic synthesis plays a vital role in elucidating their structures and understanding their formation.
  • This review consolidates current knowledge, highlighting areas for future research in natural product chemistry.