Journal ArticleDOI
How to Start a Total Synthesis from the Wieland-Miescher Ketone?
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TLDR
Modifications of the Wieland-Miescher ketone are composed of oxidation, reduction, and electrophilic or nucleophilic addition, and the introduction of substituents into α-position of C=C and C=O can also be used to modify the structure of this widely used ketone.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.read more
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Journal ArticleDOI
Biocatalytic Approaches to the Enantiomers of Wieland–Miescher Ketone and its Derivatives
Susanna Bertuletti,Ikram Bayout,Ivan Bassanini,Erica Elisa Ferrandi,Nassima Bouzemi,Daniela Monti,Sergio Riva +6 more
Journal ArticleDOI
Divergent total synthesis of marine meroterpenoids (+)-dysidavarones A–C
TL;DR: In this article , a divergent enantioselective total synthesis of marine sesquiterpene quinone meroterpenoids (+)-dysidavarones A-C (1-3) was reported.
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