An approach towards the synthesis of codinaeopsin derivatives as uniques tryptophan-polyketide anti-malarial compounds / Ummu Umairah M Hatta

In this study, codinaeopsin was chosen as our synthetic target compound due to its unique tryptophan-tetramic acid, pyrrolidinone structure. Codinaeopsin was isolated from biological source which is white yemeri trees and obtaining the continuous supply of codinaeopsin is problematic due to the scar...

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Main Author:	M Hatta, Ummu Umairah
Format:	Thesis
Language:	English
Published:	2024
Subjects:	Acids and bases
Online Access:	https://ir.uitm.edu.my/id/eprint/107133/1/107133.pdf
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id	my-uitm-ir.107133
record_format	uketd_dc
spelling	my-uitm-ir.1071332024-12-04T08:24:29Z An approach towards the synthesis of codinaeopsin derivatives as uniques tryptophan-polyketide anti-malarial compounds / Ummu Umairah M Hatta 2024 M Hatta, Ummu Umairah Acids and bases In this study, codinaeopsin was chosen as our synthetic target compound due to its unique tryptophan-tetramic acid, pyrrolidinone structure. Codinaeopsin was isolated from biological source which is white yemeri trees and obtaining the continuous supply of codinaeopsin is problematic due to the scarcity of product origin. Over the decade, there is only one successful total synthesis of codinaeopsin was reported involving a lengthy step. Thus, a new synthetic route had been developed to overcome the problem. A series of successive functional group modifications was performed which began with esterification of L-tryptophan by using methanol and thionyl chloride (100%), followed by condensation of the methyl ester utilizing the methyl malonyl chloride to furnish an intermediate diester. This diester is then reacted with sodium methoxide to furnish β,βdiketo pyrrolidinone, a crucial diketo pyrrolidinone ring template via Dieckmann cyclization reaction. Lastly, the tetramic acid type compound is achieved by decarboxylation of the β,β-diketo pyrrolidinone employing acetonitrile. All compounds were synthesized in moderate to good yield in 4 steps with an overall yield of 34.05%. Nevertheless, different pyrrolidinone-type compounds from different hydrazine salts were synthesized via hydrazination and all the compounds were produced in low to good yields. In brief, this research was designed to provide intriguing new pathways to prepare tetramic acid carbon skeleton of codinaeopsin and minimize the cost and shorten the route for synthesizing tetramic acid. 2024 Thesis https://ir.uitm.edu.my/id/eprint/107133/ https://ir.uitm.edu.my/id/eprint/107133/1/107133.pdf text en public masters Universiti Teknologi MARA (UiTM) Faculty of Applied Science
institution	Universiti Teknologi MARA
collection	UiTM Institutional Repository
language	English
topic	Acids and bases
spellingShingle	Acids and bases M Hatta, Ummu Umairah An approach towards the synthesis of codinaeopsin derivatives as uniques tryptophan-polyketide anti-malarial compounds / Ummu Umairah M Hatta
description	In this study, codinaeopsin was chosen as our synthetic target compound due to its unique tryptophan-tetramic acid, pyrrolidinone structure. Codinaeopsin was isolated from biological source which is white yemeri trees and obtaining the continuous supply of codinaeopsin is problematic due to the scarcity of product origin. Over the decade, there is only one successful total synthesis of codinaeopsin was reported involving a lengthy step. Thus, a new synthetic route had been developed to overcome the problem. A series of successive functional group modifications was performed which began with esterification of L-tryptophan by using methanol and thionyl chloride (100%), followed by condensation of the methyl ester utilizing the methyl malonyl chloride to furnish an intermediate diester. This diester is then reacted with sodium methoxide to furnish β,βdiketo pyrrolidinone, a crucial diketo pyrrolidinone ring template via Dieckmann cyclization reaction. Lastly, the tetramic acid type compound is achieved by decarboxylation of the β,β-diketo pyrrolidinone employing acetonitrile. All compounds were synthesized in moderate to good yield in 4 steps with an overall yield of 34.05%. Nevertheless, different pyrrolidinone-type compounds from different hydrazine salts were synthesized via hydrazination and all the compounds were produced in low to good yields. In brief, this research was designed to provide intriguing new pathways to prepare tetramic acid carbon skeleton of codinaeopsin and minimize the cost and shorten the route for synthesizing tetramic acid.
format	Thesis
qualification_level	Master's degree
author	M Hatta, Ummu Umairah
author_facet	M Hatta, Ummu Umairah
author_sort	M Hatta, Ummu Umairah
title	An approach towards the synthesis of codinaeopsin derivatives as uniques tryptophan-polyketide anti-malarial compounds / Ummu Umairah M Hatta
title_short	An approach towards the synthesis of codinaeopsin derivatives as uniques tryptophan-polyketide anti-malarial compounds / Ummu Umairah M Hatta
title_full	An approach towards the synthesis of codinaeopsin derivatives as uniques tryptophan-polyketide anti-malarial compounds / Ummu Umairah M Hatta
title_fullStr	An approach towards the synthesis of codinaeopsin derivatives as uniques tryptophan-polyketide anti-malarial compounds / Ummu Umairah M Hatta
title_full_unstemmed	An approach towards the synthesis of codinaeopsin derivatives as uniques tryptophan-polyketide anti-malarial compounds / Ummu Umairah M Hatta
title_sort	approach towards the synthesis of codinaeopsin derivatives as uniques tryptophan-polyketide anti-malarial compounds / ummu umairah m hatta
granting_institution	Universiti Teknologi MARA (UiTM)
granting_department	Faculty of Applied Science
publishDate	2024
url	https://ir.uitm.edu.my/id/eprint/107133/1/107133.pdf
_version_	1818588207357362176

An approach towards the synthesis of codinaeopsin derivatives as uniques tryptophan-polyketide anti-malarial compounds / Ummu Umairah M Hatta

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