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

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.

Abstract

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.

Metadata

Item Type: Thesis (Masters)
Creators:
Creators
Email / ID Num.
Syed Monudeen Khan, Sharifah Edayu
2008263028
Contributors:
Contribution
Name
Email / ID Num.
Thesis advisor
Hamzah, Ahmad Sazali (Professor Dr.)
UNSPECIFIED
Thesis advisor
Bathich, Yaser (Dr)
UNSPECIFIED
Thesis advisor
Shaameri, Zurina (Professor Madya Dr.)
UNSPECIFIED
Subjects: Q Science > QH Natural history - Biology > Bioactive compounds
Divisions: Universiti Teknologi MARA, Shah Alam > Faculty of Applied Sciences
Programme: Master of Science
Keywords: Dysidamide C; Synthesis; Skeletal structure
Date: May 2013
URI: https://ir.uitm.edu.my/id/eprint/15534
Edit Item
Edit Item

Download

[thumbnail of 15534.pdf] Text
15534.pdf

Download (2MB)

Digital Copy

Digital (fulltext) is available at:

Physical Copy

Physical status and holdings:
Item Status:

ID Number

15534

Indexing

Statistic

Statistic details