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 s...

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Main Author:	Syed Monudeen Khan, Sharifah Edayu
Format:	Thesis
Language:	English
Published:	2013
Subjects:	Bioactive compounds
Online Access:	http://ir.uitm.edu.my/id/eprint/15534/ http://ir.uitm.edu.my/id/eprint/15534/1/TM_SHARIFAH%20EDAYU%20SYED%20MONUDEEN%20KHAN%20AS%2013_5.pdf

id	uitm-15534
recordtype	eprints
spelling	uitm-155342016-12-06T02:32:37Z http://ir.uitm.edu.my/id/eprint/15534/ An approach towards the synthesis of Dysidamide C and its derivatives / Sharifah Edayu Syed Monudeen Khan 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 Thesis NonPeerReviewed text en http://ir.uitm.edu.my/id/eprint/15534/1/TM_SHARIFAH%20EDAYU%20SYED%20MONUDEEN%20KHAN%20AS%2013_5.pdf Syed Monudeen Khan, Sharifah Edayu (2013) An approach towards the synthesis of Dysidamide C and its derivatives / Sharifah Edayu Syed Monudeen Khan. Masters thesis, Universiti Teknologi MARA.
repository_type	Digital Repository
institution_category	Local University
institution	Universiti Teknologi MARA
building	UiTM Institutional Repository
collection	Online Access
language	English
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
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
publishDate	2013
url	http://ir.uitm.edu.my/id/eprint/15534/ http://ir.uitm.edu.my/id/eprint/15534/1/TM_SHARIFAH%20EDAYU%20SYED%20MONUDEEN%20KHAN%20AS%2013_5.pdf
first_indexed	2023-09-18T22:54:04Z
last_indexed	2023-09-18T22:54:04Z
_version_	1777417736290304000

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

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