Topic
Wieland–Miescher ketone
About: Wieland–Miescher ketone is a research topic. Over the lifetime, 88 publications have been published within this topic receiving 938 citations. The topic is also known as: 8a-Methyl-3,4,7,8-tetrahydro-2H-naphthalene-1,6-dione.
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TL;DR: In this paper, a procedure for recyclingable asymmetric cyclization leading to optically active Wieland-Miescher ketone analogue was developed employing D-phenylalanine and D-CSA in [hmim]PF 6 and dimethylimidazolidinone in 81% chemical yield and 74% enantiomeric excess in average after five uses.
Abstract: A procedure for recyclable asymmetric cyclization leading to optically active Wieland-Miescher ketone analogue has been developed employing D-phenylalanine and D-CSA in [hmim]PF 6 and dimethylimidazolidinone in 81% chemical yield and 74% enantiomeric excess in average after five uses. A Hajos-Wiechert ketone analogue was also synthesized in a similar manner.
2 citations
TL;DR: An optimized procedure for Wieland-Miescher Ketone synthesis using crude lipase preparations is created, characterizing both reaction yield and enantiomeric excess and proposing a general absorbance-based screening methodology for assessing biocatalytic potential of crude enzyme preparations for synthesis of WMK.
Abstract: Lipases, a versatile class of biocatalysts, have been shown to function in non-aqueous media/organic solvents and to possess “promiscuous” catalytic activity for a wide range of organic transformations. In this study, we explored the biocatalytic properties of a library of commercially available lipases by screening them for catalysis of a one-pot synthesis of Wieland–Miescher ketone, an important intermediate in the synthesis of biologically active compounds such as steroids and terpenoids, from methyl vinyl ketone and 2-methyl-1,3-cyclohexanedione. As a direct outgrowth of this screen, we created an optimized procedure for Wieland–Miescher ketone (WMK) synthesis using crude lipase preparations, characterizing both reaction yield and enantiomeric excess. We also identified principal components of the crude lipase mixture through proteomics and present evidence for a non-lipolytic origin of the observed catalysis. Finally, using the optimized conditions developed in this study, we propose a general absorbance-based screening methodology for assessing biocatalytic potential of crude enzyme preparations for synthesis of WMK.
2 citations
TL;DR: A novel synthesis of the title compound has been accomplished starting with alcohol (3) which in turn was prepared from the Wieland-Miescher ketone (1), which after reduction, mesylation, and demesylation afforded the unsaturated ester as discussed by the authors.
2 citations
TL;DR: 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.
2 citations
Journal Article•
TL;DR: Synthese des composes du titre a partir de l'acide dimethoxy-2,6 benzoique via la cyclisation aldol asymetrique des derives oxobutyl- and oxopentyl- de la cyclohexanedione-1,3 intermediaire as mentioned in this paper.
Abstract: Synthese des composes du titre a partir de l'acide dimethoxy-2,6 benzoique via la cyclisation aldol asymetrique des derives oxobutyl- et oxopentyl- de la cyclohexanedione-1,3 intermediaire
2 citations