Showing papers on "Wieland–Miescher ketone published in 2015"

One-pot synthesis of Wieland–Miescher ketone by enzymes

Abstract: We first report that lipase from porcine pancreas catalyzed Robinson annulation in the organic media to synthesize the Wieland–Miescher ketone. The promiscuous catalytic activity of lipase in the Robinson reaction is due to an important role played by lipase activity in both the Michael addition and Aldol reaction.

Synthesis of Selected Phenylalanine Esters C1 to C4 and their Catalytic Activity on the Preparation of a Wieland Miescher Intermediate Using Acidic Media

Abstract: The Wieland Miescher intermediate is used in the synthesis of a range of antitumour, antiviral, antimicrobial and antineurodegenerative drugs. Our work outlines the synthesis of a range of surfactant esters derived from the amino acid phenylalanine and which have been used as asymmetric catalysts to synthesize the key intermediate leading to the Wieland Miescher ketone. These reactions were carried out in water under acidic media. Satisfactory yields of up to 75% were obtained in generating the intermediate, and 92% of the subsequent Wieland Miescher Ketone was obtained with an enantiomeric purity of 72-73% e.e selective to the S-isomer. Keywords: Wieland-Miescher, Phenylalanine esters, CTAB, CMC, Methyl Vinyl Ketone, 2-Methylcyclohexane-1,3-dione

Enantiodivergent Synthesis of Wieland—Miescher Ketone Analogue Mediated by a Chiral Pyridinylmethylamine Derivative.

Abstract: The title compound is synthesized by the intramolecular aldol reaction of trione (I) mediated by a chiral pyridinylmethyl amine in the presence of trifluoroacetic acid.