Related Experiment Video
Updated: Jun 7, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Synthesis of Rapicone Based on Acyl Ketene-Alkyne Cycloaddition
Erandi Liyanage Perera1, Daesung Lee1
1Department of Chemistry, University of Illinois Chicago, 845 West Taylor Street, Chicago, Illinois 60607, United States.
Researchers developed a concise 7-step synthesis for rapicone, utilizing an iron-catalyzed oxidation to create a key ynone intermediate. This efficient method achieves a 9.4% overall yield for the total synthesis of rapicone.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Total synthesis of complex natural products like rapicone presents significant challenges.
- Developing efficient and concise synthetic routes is crucial for accessing biologically active molecules.
Purpose of the Study:
- To report a novel and concise total synthesis of rapicone.
- To establish an efficient strategy for constructing the ynone intermediate.
Main Methods:
- Fe(III)/TEMPO-catalyzed aerobic oxidation of a 1,3-dihydroisobenzofuran to form a keto aldehyde.
- Formal [4 + 2] cycloaddition reaction between an acyl ketene and an alkynone.
Main Results:
- A 7-step total synthesis of rapicone was achieved.
- The key ynone intermediate was successfully formed via ether oxidation.
- An overall yield of 9.4% was obtained for the total synthesis.
Conclusions:
- The developed synthetic route is concise and efficient for rapicone production.
- The Fe(III)/TEMPO-catalyzed oxidation is a key step enabling the synthesis.
- This work provides a valuable method for the synthesis of rapicone and related compounds.
More Related Videos
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
09:35Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Related Concept Videos
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Cycloaddition Reactions: Overview