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Related Concept Videos

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...
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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 antagonists are called...
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Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
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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...
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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...
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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
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Related Experiment Video

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Applications of Liquid-Chromatography Tandem Mass Spectrometry in Natural Products Research: Tropane Alkaloids as a Case Study
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Total synthesis of (±)-chamobtusin A.

Hikaru Suzuki1, Sakae Aoyagi

  • 1School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.

Chemical Communications (Cambridge, England)
|June 3, 2011
PubMed
Summary

Researchers describe the total synthesis of chamobtusin A, a diterpenoid alkaloid from Pinales. The study highlights key steps like stereoselective Michael addition and oxidative manipulation for pyrrole ring formation.

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Phytochemistry

Background:

  • Chamobtusin A is a unique diterpenoid alkaloid.
  • It is the first diterpenoid alkaloid isolated from the whole Pinales.
  • Understanding its structure and properties requires efficient synthesis methods.

Purpose of the Study:

  • To achieve the total synthesis of chamobtusin A.
  • To develop and showcase novel synthetic strategies for complex diterpenoid alkaloids.
  • To provide a reliable route for accessing chamobtusin A for further studies.

Main Methods:

  • Stereoselective intramolecular Michael addition for key stereocenter installation.
  • Oxidative manipulation for the construction of the 2H-pyrrole ring.

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  • Multi-step total synthesis employing modern organic chemistry techniques.

    • Main Results:

    • Successful total synthesis of chamobtusin A was accomplished.
    • The key stereocenter was efficiently installed using the designed Michael addition.
    • The 2H-pyrrole moiety was successfully constructed via oxidative manipulation.

    Conclusions:

    • The total synthesis of chamobtusin A is now feasible.
    • The developed synthetic route provides access to this Pinales-derived diterpenoid alkaloid.
    • This work contributes to the field of natural product synthesis and methodology development.