Synthesis and decarboxylation of benzylated B,B-diketoester towards the synthesis of preussin / Muhamad Syazwan Othman

• Main Author: Othman, Muhamad Syazwan
• Format: Thesis
• Language: English
• Published: 2010
• Online Access: https://ir.uitm.edu.my/id/eprint/101195/1/101195%20.pdf; https://ir.uitm.edu.my/id/eprint/101195/
• Institution: Universiti Teknologi Mara

This thesis describes a simple and efficient methodology for the synthesis and decarboxylation of benzylated B,B-diketoester, 5-benzyl-2,4-dioxopyrrolidine-3-carboxylate towards the synthesis of preussin. Preussin is a pyrrolidinol alkaloid which originally understood to have significant antifungal activity. Preussin therefore provide an interesting lead structure for the design of novel antitumor drugs. Thus, in this synthesis, the key compound, 5-benzyl-pyrrolidine-2,4-dione was synthesis by a few effective steps. The initial step was the esterification to produce a product that can be coupled with methyl malonate potassium salt. The product from the coupling was then cyclized to obtain the P,P-diketoester mentioned. Lastly, decarboxylation step was performed to remove the ester group, thus, producing the key compound towards the synthesis of preussin. All products synthesized were purified and then characterized using FTIR, ^-NMR and 13C-NMR spectroscopy for structure confirmation.