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

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...

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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/
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spelling my.uitm.ir.1011952024-09-12T03:23:09Z https://ir.uitm.edu.my/id/eprint/101195/ Synthesis and decarboxylation of benzylated B,B-diketoester towards the synthesis of preussin / Muhamad Syazwan Othman Othman, Muhamad Syazwan 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. 2010 Thesis NonPeerReviewed text en https://ir.uitm.edu.my/id/eprint/101195/1/101195%20.pdf Synthesis and decarboxylation of benzylated B,B-diketoester towards the synthesis of preussin / Muhamad Syazwan Othman. (2010) Degree thesis, thesis, Universiti Teknologi MARA (UiTM). <http://terminalib.uitm.edu.my/101195.pdf>
institution Universiti Teknologi Mara
building Tun Abdul Razak Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Mara
content_source UiTM Institutional Repository
url_provider http://ir.uitm.edu.my/
language English
description 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.
format Thesis
author Othman, Muhamad Syazwan
spellingShingle Othman, Muhamad Syazwan
Synthesis and decarboxylation of benzylated B,B-diketoester towards the synthesis of preussin / Muhamad Syazwan Othman
author_facet Othman, Muhamad Syazwan
author_sort Othman, Muhamad Syazwan
title Synthesis and decarboxylation of benzylated B,B-diketoester towards the synthesis of preussin / Muhamad Syazwan Othman
title_short Synthesis and decarboxylation of benzylated B,B-diketoester towards the synthesis of preussin / Muhamad Syazwan Othman
title_full Synthesis and decarboxylation of benzylated B,B-diketoester towards the synthesis of preussin / Muhamad Syazwan Othman
title_fullStr Synthesis and decarboxylation of benzylated B,B-diketoester towards the synthesis of preussin / Muhamad Syazwan Othman
title_full_unstemmed Synthesis and decarboxylation of benzylated B,B-diketoester towards the synthesis of preussin / Muhamad Syazwan Othman
title_sort synthesis and decarboxylation of benzylated b,b-diketoester towards the synthesis of preussin / muhamad syazwan othman
publishDate 2010
url https://ir.uitm.edu.my/id/eprint/101195/1/101195%20.pdf
https://ir.uitm.edu.my/id/eprint/101195/
_version_ 1811598196625899520
score 13.211869

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