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Related Concept Videos

UV–Vis Spectroscopy: Woodward–Fieser Rules01:29

UV–Vis Spectroscopy: Woodward–Fieser Rules

UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the contributions...
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...
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.
[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.
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: 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...

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Related Experiment Video

Updated: May 29, 2026

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

Proposed Biosynthesis of the Complex Ring-Fused Diterpene Rameswaralide. Mechanistic Insights Using Density

Di Wang1, Tao Zhou1, Rui Wang1

  • 1Nottingham Ningbo China Beacons of Excellence Research and Innovation Institute, Key Laboratory for Carbonaceous Waste Processing and Process Intensification Research of Zhejiang Province, Department of Chemical and Environmental Engineering, The University of Nottingham Ningbo China, 199 Taikang East Road, Ningbo 315100, P. R. China.

The Journal of Organic Chemistry
|May 28, 2026
PubMed
Summary

Computational studies reveal that coral metabolite rameswaralide biosynthesis primarily involves a [4 + 3] transannular cyclization of a polyene macrocycle. This key step, derived from a furanocembranoid precursor, dictates the formation of its complex ring-fused structure.

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Area of Science:

  • Natural Product Biosynthesis
  • Computational Chemistry
  • Organic Chemistry

Background:

  • Coral metabolites like rameswaralide possess complex ring-fused structures.
  • Understanding the biosynthesis of such natural products is crucial for synthetic chemistry and drug discovery.

Purpose of the Study:

  • To elucidate the biosynthetic pathway of the coral metabolite rameswaralide.
  • To identify the key cyclization step and intermediate structures involved in rameswaralide formation.
  • To evaluate alternative proposed biosynthetic routes.

Main Methods:

  • Density functional theory (DFT) calculations using M06-2X and ωB97X-D functionals.
  • Analysis of reaction mechanisms, including transannular cyclization and rearrangements.
  • Investigation of intermediate structures and conformational preferences.

Main Results:

  • The primary pathway involves a [4 + 3] transannular cyclization of a polyene macrocycle intermediate.
  • Alternative pathways, including [4 + 2] cyclization and α-ketol rearrangement, were computationally deemed untenable.
  • The polyene macrocycle originates from a furanocembranoid precursor via oxidation, dearomatization, and ring-opening steps.
  • Protonation facilitates ring opening and conformational shifts, leading to the thermodynamically favored rameswaralide isomer.

Conclusions:

  • The [4 + 3] transannular cyclization is the most plausible key step in rameswaralide biosynthesis.
  • Computational modeling provides critical insights into complex natural product formation pathways.
  • The study clarifies the mechanism, ruling out previously suggested alternative routes.