An approach towards the synthesis of Dysidamide C and its derivatives / Sharifah Edayu Syed Monudeen Khan

Dysidamide C was chosen in this study as the synthetic target due to its unique skeletal structure and its interesting pharmacological activities. This thesis has been divided into five main sections. Chapter one is a review on our target compounds-Dysidamide C. Chapter two focus on the synthetic st...

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Main Author:	Syed Monudeen Khan, Sharifah Edayu
Format:	Thesis
Language:	English
Published:	2013
Subjects:	Bioactive compounds
Online Access:	https://ir.uitm.edu.my/id/eprint/15534/1/15534.pdf
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id	my-uitm-ir.15534
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spelling	my-uitm-ir.155342022-04-14T00:23:03Z An approach towards the synthesis of Dysidamide C and its derivatives / Sharifah Edayu Syed Monudeen Khan 2013-05 Syed Monudeen Khan, Sharifah Edayu Bioactive compounds Dysidamide C was chosen in this study as the synthetic target due to its unique skeletal structure and its interesting pharmacological activities. This thesis has been divided into five main sections. Chapter one is a review on our target compounds-Dysidamide C. Chapter two focus on the synthetic strategies of compound which have similar skeleton to Dysidamide C by different research groups, whilst chapter three consists of our synthetic works. Experimental details including the spectroscopic data are provided in chapter four and finally, future works are recommended in chapter five. Our synthetic approach towards the synthesis of Dysidamide C was divided into two different routes. The first route began by couple up readily available starting material known as glycine methyl ester and methyl malonate potassium through condensation reaction followed by Dieckmann cyclisation to give pyrolidine ring known as the p,p-diketoester. Letting p,pdiketoester undergo a series of successive chemical reactions, which include demethoxycarbonylation, dialkylation at C-3 position, olefin formation at C-5, successfully gave our desire template known as methylene ketone type of compounds, 125 (with an overall yield of 21%). For the second route, methylene ketone type of compounds, 125, was obtained in four steps using methyl acetoacetate as the starting material. The first step was known as dimethylation, followed by brominations, intercyclization reaction and finally olefin formations at C-5 (with an overall yield of 26%). This entire attempt was successfully furnished us with over 35 pyrrolidine type of compounds. Apart from that, we manage to manipulate the important intermediates 125, to produce Dysidamide C-derivative known as diesterified compound and woxazoline in 4 steps. In brief, we have developed a mild and operationally simple procedure towards the synthesis of Dysidamide C. The result extracted from this study thus far may be used to develop new scientific knowledge and remarkable findings. 2013-05 Thesis https://ir.uitm.edu.my/id/eprint/15534/ https://ir.uitm.edu.my/id/eprint/15534/1/15534.pdf text en public mphil masters Universiti Teknologi MARA Faculty of Applied Sciences Hamzah, Ahmad Sazali (Professor Dr.) Bathich, Yaser (Dr) Shaameri, Zurina (Professor Madya Dr.)
institution	Universiti Teknologi MARA
collection	UiTM Institutional Repository
language	English
advisor	Hamzah, Ahmad Sazali (Professor Dr.) Bathich, Yaser (Dr) Shaameri, Zurina (Professor Madya Dr.)
topic	Bioactive compounds
spellingShingle	Bioactive compounds Syed Monudeen Khan, Sharifah Edayu An approach towards the synthesis of Dysidamide C and its derivatives / Sharifah Edayu Syed Monudeen Khan
description	Dysidamide C was chosen in this study as the synthetic target due to its unique skeletal structure and its interesting pharmacological activities. This thesis has been divided into five main sections. Chapter one is a review on our target compounds-Dysidamide C. Chapter two focus on the synthetic strategies of compound which have similar skeleton to Dysidamide C by different research groups, whilst chapter three consists of our synthetic works. Experimental details including the spectroscopic data are provided in chapter four and finally, future works are recommended in chapter five. Our synthetic approach towards the synthesis of Dysidamide C was divided into two different routes. The first route began by couple up readily available starting material known as glycine methyl ester and methyl malonate potassium through condensation reaction followed by Dieckmann cyclisation to give pyrolidine ring known as the p,p-diketoester. Letting p,pdiketoester undergo a series of successive chemical reactions, which include demethoxycarbonylation, dialkylation at C-3 position, olefin formation at C-5, successfully gave our desire template known as methylene ketone type of compounds, 125 (with an overall yield of 21%). For the second route, methylene ketone type of compounds, 125, was obtained in four steps using methyl acetoacetate as the starting material. The first step was known as dimethylation, followed by brominations, intercyclization reaction and finally olefin formations at C-5 (with an overall yield of 26%). This entire attempt was successfully furnished us with over 35 pyrrolidine type of compounds. Apart from that, we manage to manipulate the important intermediates 125, to produce Dysidamide C-derivative known as diesterified compound and woxazoline in 4 steps. In brief, we have developed a mild and operationally simple procedure towards the synthesis of Dysidamide C. The result extracted from this study thus far may be used to develop new scientific knowledge and remarkable findings.
format	Thesis
qualification_name	Master of Philosophy (M.Phil.)
qualification_level	Master's degree
author	Syed Monudeen Khan, Sharifah Edayu
author_facet	Syed Monudeen Khan, Sharifah Edayu
author_sort	Syed Monudeen Khan, Sharifah Edayu
title	An approach towards the synthesis of Dysidamide C and its derivatives / Sharifah Edayu Syed Monudeen Khan
title_short	An approach towards the synthesis of Dysidamide C and its derivatives / Sharifah Edayu Syed Monudeen Khan
title_full	An approach towards the synthesis of Dysidamide C and its derivatives / Sharifah Edayu Syed Monudeen Khan
title_fullStr	An approach towards the synthesis of Dysidamide C and its derivatives / Sharifah Edayu Syed Monudeen Khan
title_full_unstemmed	An approach towards the synthesis of Dysidamide C and its derivatives / Sharifah Edayu Syed Monudeen Khan
title_sort	approach towards the synthesis of dysidamide c and its derivatives / sharifah edayu syed monudeen khan
granting_institution	Universiti Teknologi MARA
granting_department	Faculty of Applied Sciences
publishDate	2013
url	https://ir.uitm.edu.my/id/eprint/15534/1/15534.pdf
_version_	1783733417019441152

An approach towards the synthesis of Dysidamide C and its derivatives / Sharifah Edayu Syed Monudeen Khan

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