Related Experiment Video
Updated: Jul 19, 2026
09:04
A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Total synthesis of (+/-)-clavubicyclone
Hisanaka Ito1, Shunta Takeguchi, Takahiro Kawagishi
1School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan. itohisa@las.toyaku.ac.jp
Organic Letters
|October 6, 2006
Summary
This study details the first total synthesis of racemic clavubicyclone, a compound found in Okinawan soft coral. Key steps included Cope rearrangement for skeleton construction and Barton decarboxylation, Wittig reaction, and alkylation for functionalization.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Marine Natural Products
Background:
- Clavubicyclone is a unique compound isolated from Okinawan soft coral.
- The complex structure of clavubicyclone presents a significant synthetic challenge.
- Understanding its synthesis can aid in exploring related marine natural products.
Purpose of the Study:
- To achieve the first total synthesis of racemic clavubicyclone.
- To develop efficient synthetic routes for constructing the bicyclo[3.2.1]octane core.
- To establish methods for introducing key functional groups onto the core structure.
Main Methods:
- Cope rearrangement of a divinylcyclopropane derivative to form the bicyclo[3.2.1]octane skeleton.
- Barton decarboxylation for functional group manipulation.
- Wittig reaction for alkene formation.
- Alkylation for introducing specific substituents.
Main Results:
- Successful total synthesis of racemic clavubicyclone.
- Demonstration of Cope rearrangement as an effective strategy for the core structure.
- Validation of Barton decarboxylation, Wittig reaction, and alkylation in the synthesis.
Conclusions:
- The described synthetic route provides a viable pathway to racemic clavubicyclone.
- This synthesis opens avenues for the preparation of clavubicyclone analogs.
- The methodology can be applied to the synthesis of other complex natural products.
More Related Videos
Related Concept Videos
02:35Clausius-Clapeyron Equation
The equilibrium between a liquid and its vapor depends on the temperature of the system; a rise in temperature causes a corresponding rise in the vapor pressure of its liquid. The Clausius-Clapeyron equation gives the quantitative relation between a substance’s vapor pressure (P) and its temperature (T); it predicts the rate at which vapor pressure increases per unit increase in temperature.
01:18β-Dicarbonyl Compounds via Crossed Claisen Condensations
Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
01:45Vesicular Tubular Clusters
After budding out from the ER membrane, some COPII vesicles lose their coat and fuse with one another to form larger vesicles and interconnected tubules called vesicular tubular clusters or VTCs. These clusters constitute a compartment at the ER-Golgi interface known as ERGIC (Endoplasmic Reticulum Golgi Intermediate Compartment). The ERGIC is a mobile membrane-bound cargo transport system that sorts proteins secreted from ER and delivers them to the Golgi.
With the help of motor proteins such...
With the help of motor proteins such...
01:29The Clausius–Clapeyron Equation
The Clausius-Clapeyron equation is a fundamental principle in physical chemistry and thermodynamics that describes the relationship between a substance's vapor pressure and temperature. Named after Rudolf Clausius and Benoît Paul Émile Clapeyron, the equation is integral in predicting a substance's behavior under different temperature conditions.The Clausius-Clapeyron equation allows us to calculate how the pressure at which a liquid boils (its vapor pressure) changes as the temperature changes.
03:11Precipitation of Ions
Predicting Precipitation
The equation that describes the equilibrium between solid calcium carbonate and its solvated ions is:
The equation that describes the equilibrium between solid calcium carbonate and its solvated ions is:
01:08Esters to β-Ketoesters: Claisen Condensation Mechanism
Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the intermediate restores...