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Related Concept Videos

Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
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.
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...

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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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Published on: October 4, 2019

A macrocyclic dimeric diterpene with a C2 symmetry axis.

J Jesús Manríquez-Torres1, J Martín Torres-Valencia, René Velázquez-Jiménez

  • 1Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, km 4.5 Carretera Pachuca-Tulancingo, Mineral de la Reforma, Hidalgo, 42184 Mexico, and Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México, D.F., 07000 Mexico.

Organic Letters
|August 14, 2013
PubMed
Summary

A novel macrocyclic dimeric diterpene, schaffnerine, was isolated from Acacia schaffneri. Its unique structure and absolute configuration were determined using advanced spectroscopic and crystallographic methods.

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Area of Science:

  • Natural Product Chemistry
  • Organic Chemistry
  • Phytochemistry

Background:

  • Acacia species are known sources of diverse bioactive compounds.
  • Dimeric diterpenes with macrocyclic structures are rare in nature.
  • Understanding the chemical diversity of plant secondary metabolites is crucial.

Purpose of the Study:

  • To isolate and characterize a novel macrocyclic dimeric diterpene from Acacia schaffneri.
  • To determine the absolute configuration and preferred conformation of the isolated compound.
  • To contribute to the understanding of diterpene biosynthesis and structural diversity.

Main Methods:

  • Isolation and purification of the compound using chromatographic techniques.
  • Structure elucidation via comprehensive spectroscopic data analysis (NMR, MS).
  • Determination of absolute configuration using vibrational circular dichroism (VCD) spectroscopy and single-crystal X-ray diffraction.

Main Results:

  • Isolation of an unprecedented macrocyclic dimeric diterpene, named schaffnerine.
  • Full characterization of schaffnerine, including its complex stereochemistry.
  • Confirmation of the absolute configuration using computational chemistry (DFT) and X-ray crystallography.

Conclusions:

  • Schaffnerine represents a new class of macrocyclic dimeric diterpenes.
  • The study highlights the potential of Acacia schaffneri as a source of novel natural products.
  • The applied methodologies provide a robust framework for characterizing complex natural products.