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How to Start a Total Synthesis from the Wieland-Miescher Ketone?

[ Vol. 16 , Issue. 3 ]

Author(s):

Zai-Qun Liu *   Pages 328 - 341 ( 14 )

Abstract:


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.

Keywords:

Wieland-Miescher ketone, total synthesis, structural modification, screening chiral organocatalysts, bioactive molecules, novel protocols.

Affiliation:

Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021

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