Related Experiment Video
Updated: May 14, 2026
07:04
A High-performance Liquid Chromatography Measurement of Kynurenine and Kynurenic Acid: Relating Biochemistry to Cognition and Sleep in Rats
Published on: August 19, 2018
Total synthesis of kopsinine
Jian Xie1, Amanda L Wolfe, Dale L Boger
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Organic Letters
|February 9, 2013
Summary
This study details a novel synthesis of kopsinine using a powerful cycloaddition cascade and a unique SmI(2)-promoted reaction. This approach efficiently constructs the complex hexacyclic core structure.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Total Synthesis
Background:
- Kopsinine is a complex natural product with a challenging hexacyclic structure.
- Efficient synthetic routes to kopsinine are crucial for further biological studies.
Purpose of the Study:
- To detail a novel and divergent total synthesis of kopsinine.
- To showcase a powerful intramolecular cycloaddition cascade and a unique SmI(2)-promoted reaction.
Main Methods:
- Intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of an 1,3,4-oxadiazole.
- Samarium(II) iodide (SmI(2))-promoted transannular cyclization.
- Divergent synthetic strategy.
Main Results:
- Successful construction of the bicyclo[2.2.2]octane core.
- Efficient formation of the hexacyclic ring system of kopsinine.
- Demonstration of a unique SmI(2)-promoted cyclization.
Conclusions:
- The developed synthetic strategy provides an efficient route to kopsinine.
- The novel cascade and SmI(2)-promoted reactions are powerful tools for complex molecule synthesis.
- This work expands the synthetic methodologies in organic chemistry.
More Related Videos
Related Concept Videos
01:29Drugs Affecting Neurotransmitter Synthesis
Drugs affecting neurotransmitter synthesis can impact the adrenergic neuron and the synthesis of neurotransmitters. For example, α-methyltyrosine and carbidopa target specific enzymes involved in catecholamine synthesis. α-methyltyrosine inhibits the enzyme tyrosine hydroxylase, which converts tyrosine into dopamine. By blocking this enzyme, α-methyltyrosine reduces dopamine production and other catecholamines. Carbidopa, on the other hand, inhibits the enzyme dopa decarboxylase, which converts...
01:27Combined Effects of Drugs: Synergism
Synergism is a useful mechanism where combining two or more drugs is more effective than each constituent used alone. Such combinations are also called supra-additive interactions. The drugs collectively enhance the final therapeutic effect by acting on different targets. Another advantage is that the low dose of each constituent drug is sufficient to achieve the desired effect. This helps reduce the duration of therapy and lower the adverse effects of these drugs.
Such synergistic combinations...
Such synergistic combinations...
01:15Opioid Analgesics: Synthetic and Semisynthetic Opioids
Synthetic and semisynthetic opioids are pivotal in pain management and tackling opioid addiction. Semisynthetic opioids, including morphinans (morphine derivatives), oxycodone, oxymorphone, hydrocodone, and hydromorphone, have improved pharmacokinetic profiles compared to morphine. Additionally, heroin and 6-MAM (6-Monoacetylmorphine) show better CNS penetration than morphine due to heightened lipid solubility. Hydromorphone, a potent opioid, undergoes hepatic metabolism to form the active...
01:20Opioid Analgesics: Morphine and Other Natural Cogeners
Opioids are a class of drugs that mimic endogenous opioid peptides and act on opioid receptors, and help in pain relief. These compounds are classified as natural, synthetic, or semi-synthetic. Natural opioids, like morphine, codeine, and thebaine, are derived from the opium poppy plant (Papaver somniferum or Papaver album) and are termed opiates. Synthetic opioids are artificial, while semi-synthetic opioids combine natural and synthetic compounds. Morphine, a prototypical opioid, possesses a...
01:30Combined Effects of Drugs: Antagonism
The combined effects of drugs can result in various interactions, of which an important type is antagonism. Antagonism is a mechanism where one drug inhibits or counteracts the effects of another drug. Antagonism can occur through various means, including receptor binding, allosteric modulation, functional interaction, chemical reactions, and pharmacokinetic processes.
The most common type is receptor antagonism, where one drug acts as an antagonist to block the effects of another drug by...
The most common type is receptor antagonism, where one drug acts as an antagonist to block the effects of another drug by...
01:16Adrenergic Agonists: Chemistry and Structure-Activity Relationship
Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...