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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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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.
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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.
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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.
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Updated: Jun 16, 2025

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Neo-5,10-seco-clerodane diterpenoids from Schnabelia terniflora.

Yi Chen1, Xu-Lan Bai1, Ting-Ting Du1

  • 1Key Laboratory of Standardization of Chinese Medicines, Ministry of Education, Institute of Chinese Materia Medica of Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China.

Fitoterapia
|August 17, 2024
PubMed
Summary

Researchers isolated 15 diterpenoids from Schnabelia terniflora, including novel compounds. Diterpenoids 2 and 14 exhibited moderate cytotoxicity against lung and gastric cancer cell lines.

Keywords:
Biosynthetic pathwayCytotoxic activityLamiaceaeNeo-5,10-seco-clerodaneSchnabelia terniflora

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Area of Science:

  • Natural Product Chemistry
  • Phytochemistry
  • Organic Chemistry

Background:

  • Schnabelia terniflora is a plant source of diverse chemical compounds.
  • Diterpenoids are a class of natural products with various biological activities.
  • Understanding the chemical constituents of medicinal plants is crucial for drug discovery.

Purpose of the Study:

  • To isolate and characterize new diterpenoids from Schnabelia terniflora.
  • To investigate the cytotoxic activities of the isolated diterpenoids against cancer cell lines.
  • To elucidate the structures of novel compounds using advanced spectroscopic techniques.

Main Methods:

  • Isolation of compounds using chromatographic techniques.
  • Structure elucidation via extensive spectroscopic analysis (NMR, MS).
  • Single-crystal X-ray diffraction and electronic circular dichroism (ECD) calculations for structural confirmation.

Main Results:

  • Isolation of 15 diterpenoids: 3 new neo-5,10-seco-clerodane diterpenoids (1-3), 4 new acetal analogues (4-7), 1 new etherified labdane diterpenoid (8), and 7 known diterpenoids (9-15).
  • Compounds 2 and 3 are the first reported neo-5,10-seco-clerodane diterpenoids with pyrrole-2,5-dione and pyrrolidine-2,5-dione moieties, respectively.
  • Compounds 2 and 14 demonstrated moderate cytotoxic activity against non-small-cell lung cancer (A549, H460) and gastric cancer (HGC27, AGS) cell lines.

Conclusions:

  • The study successfully identified novel diterpenoids from Schnabelia terniflora.
  • The isolated compounds, particularly 2 and 14, show potential as cytotoxic agents against specific cancer types.
  • Further research into the biosynthetic pathways and structure-activity relationships of these diterpenoids is warranted.