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