Related Experiment Video
Updated: Dec 30, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
How to Start a Total Synthesis from the Wieland-Miescher Ketone?
1Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, China.
Background:
The Wieland-Miescher ketone consists of a couple of enantiomers of 9-methyl- Δ5(10)-octalin-1,6-dione, in which the configuration at 9-position is S- or R-type. The Robinson annulation of 2-methyl-1,3-cyclohexanedione with methyl vinyl ketone is able to afford the Wieland-Miescher ketone. As widely used in the total synthesis, the Wieland-Miescher ketone is treated at the beginning of total synthesis, and protocols for treating the Wieland-Miescher ketone are worthy to be addressed.
Objective:
The presented review provides the progress of the usage of Wieland-Miescher ketone for the total synthesis, while treatments on C=C and C=O in the Wieland-Miescher ketone at the beginning of total synthesis are exemplified herein.
Conclusion:
Modifications of the Wieland-Miescher ketone are composed of oxidation, reduction, and electrophilic or nucleophilic addition. In addition, protection of non-conjugated C=O with glycol or protection of conjugated C=O with ethanedithiol, and the introduction of substituents into α-position of C=C can also be used to modify the structure of the Wieland-Miescher ketone. It is reasonably believed that many novel strategies will be found to treat the Wieland-Miescher ketone in the future total synthesis.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Related Concept Videos
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Esters to β-Ketoesters: Claisen Condensation Mechanism