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Related Concept Videos

Combined Effects of Drugs: Synergism01:27

Combined 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...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Drug Biotransformation: Overview01:16

Drug Biotransformation: Overview

Pharmaceutical substances known as xenobiotics are predominantly lipophilic and nonionized. This enables them to permeate lipid bilayers, such as cell membranes, and interact with intracellular target receptors. Lipophilic drugs have an advantage in crossing biological barriers and reaching their intended sites of action. However, lipophilic drugs often have a restricted capacity for renal expulsion or elimination from the body. When these drugs enter the kidneys and undergo glomerular...
Drug Biotransformation: Overview01:28

Drug Biotransformation: Overview

Biotransformation, also known as drug metabolism, is a vital physiological process that chemically alters drugs, facilitating their elimination from the body and terminating their action. This process involves two main phases: phase I and phase II reactions. Phase I reactions, including oxidation, reduction, and hydrolysis, introduce or unmask polar functional groups on the drug molecule, thereby increasing its water solubility. By enhancing water solubility, the drug becomes more hydrophilic...
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...
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,...

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Related Experiment Video

Updated: May 25, 2026

Construction of Cyclic Cell-Penetrating Peptides for Enhanced Penetration of Biological Barriers
10:12

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Published on: September 19, 2022

Total synthesis of (+)-cyperolone.

Philipp Klahn1, Alexander Duschek, Clémence Liébert

  • 1Organic Chemistry, Bergische Universität Wuppertal, Gaussstr. 20, 42119 Wuppertal, Germany.

Organic Letters
|February 14, 2012
PubMed
Summary

Researchers achieved the total synthesis of (+)-cyperolone, a sesquiterpenoid from Cyperus rotundus. This complex molecule was built using a 15-step process starting from (R)-(-)-carvone.

Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis

Background:

  • (+)-cyperolone is an eudesmane-derived sesquiterpenoid isolated from Cyperus rotundus.
  • Sesquiterpenoids are a class of terpenes derived from three isoprene units.

Purpose of the Study:

  • To describe the first total synthesis of (+)-cyperolone.
  • To establish a reliable synthetic route for this important natural product.

Main Methods:

  • De novo synthesis starting from (R)-(-)-carvone.
  • A 15-step synthetic sequence.
  • Platinum-catalyzed cycloisomerization of a 3-silyloxy-1,5-enyne intermediate to form the bicyclic core.

Main Results:

  • Successful completion of the total synthesis of (+)-cyperolone.

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  • Efficient construction of the eudesmane core structure.
  • Demonstration of a novel synthetic strategy.

    • Conclusions:

    • The developed synthetic route provides access to (+)-cyperolone.
    • The platinum-catalyzed cycloisomerization is a key step for rapid core construction.
    • This synthesis opens avenues for further exploration of sesquiterpenoid chemistry.