Related Experiment Video
Updated: Jan 6, 2026
12:06
Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
Published on: October 19, 2017
7.8K
Total Synthesis of (-)-Phomoarcherin C
Dattatraya H Dethe1, Boda VijayKumar1
1Department of Chemistry , Indian Institute of Technology , Kanpur 208016 , India.
The Journal of Organic Chemistry
|October 11, 2019
Summary
Researchers report the first total synthesis of the chroman meroterpenoid (-)-phomoarcherin C. This efficient strategy provides access to related natural products.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Chroman meroterpenoids are a class of natural products with potential biological activities.
- The total synthesis of these complex molecules presents significant challenges.
Purpose of the Study:
- To achieve the first total synthesis of (-)-phomoarcherin C.
- To develop an efficient and atom-economical synthetic strategy.
Main Methods:
- Phenyl boronic acid-mediated 6π-electrocyclization
- Stereospecific hydrogenation driven by thermodynamic conformational stability
- Regioselective formylation
Main Results:
- Successful and efficient total synthesis of (-)-phomoarcherin C.
- Demonstration of key synthetic transformations including electrocyclization, hydrogenation, and formylation.
Conclusions:
- The developed synthetic strategy is short and atom-economical.
- This approach provides access to (-)-phomoarcherin C and related chroman meroterpenoids.
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Related Concept Videos
01:16Adrenergic Agonists: Chemistry and Structure-Activity Relationship
3.8K
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...
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...
3.8K
01:29Cholinergic Antagonists: Chemistry and Structure-Activity Relationship
2.6K
Cholinergic antagonists bind to cholinergic receptors and limit the effects of acetylcholine and other cholinergic agonists. Based on the specific cholinergic receptor affinity, these antagonists are classified as muscarinic or nicotinic. Anticholinergics interrupt parasympathetic innervations while sympathetic innervations remain uninterrupted. Muscarinic antagonists are also called 'muscarinic antagonists', 'antimuscarinics', or 'parasympatholytics'. Nicotinic...
2.6K
01:31Direct-Acting Cholinergic Agonists: Pharmacokinetics
1.8K
Direct-acting cholinergic agonists, such as synthetic choline esters and naturally occurring alkaloids, exert their effects by enhancing the actions of acetylcholine and stimulating the parasympathetic nervous system. Synthetic choline esters share structural similarities with acetylcholine. For example, they have a positively charged quaternary ammonium or onium group, contributing to their hydrophilic characteristics. As a result, they are poorly absorbed in the body through oral...
1.8K
01:27Synthesis of Phosphatidylcholine in the ER Membrane
4.0K
The ER synthesizes lipids for building cell membranes and performing cellular functions such as energy storage and signaling. The lipid synthesis machinery embedded in the ER membrane primarily collects all reactants from the cytosol. Following synthesis, the secretory pathway and the ER contact sites distribute these lipids to other cellular organelles. Additionally, the energy-rich triacylglycerides are transported from the ER via lipid droplets.
The major components of all eukaryotic cell...
The major components of all eukaryotic cell...
4.0K
01:22Direct-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship
1.9K
Cholinergic agonists or cholinomimetics mimic the action of acetylcholine to stimulate the parasympathetic nervous system. They are categorized into direct-acting and indirect-acting agents. The direct-acting cholinergic drugs induce the parasympathetic response by directly binding to the muscarinic or nicotine receptors. In comparison, the indirect-acting cholinergic drugs prevent acetylcholine hydrolysis, indirectly contributing to the extended parasympathetic response.
The direct-acting...
The direct-acting...
1.9K
01:07Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
3.6K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.6K