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Synthetic studies towards the total synthesis of Zopfiellamide A / Nor Saliyana Jumali

In this study, Zopfiellamide A was chosen as a target molecule due to its unique structure and its pharmacological importance. The synthetic strategy moving towards the synthesis of Zopfiellamide A was divided accordingly based on the C-5 and C-3 substitution groups. The first approached was focused...

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Main Author: Jumali, Nor Saliyana
Format: Book Section
Language:English
Published: Institute of Graduate Studies, UiTM 2016
Subjects:
Malaysia
Animal biochemistry
Online Access:http://ir.uitm.edu.my/id/eprint/20026/1/ABS_NOR%20SALIYANA%20JUMALI%20TDRA%20VOL%2010%20IGS%2016.pdf
http://ir.uitm.edu.my/id/eprint/20026/
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spelling my.uitm.ir.200262018-06-11T03:31:08Z http://ir.uitm.edu.my/id/eprint/20026/ Synthetic studies towards the total synthesis of Zopfiellamide A / Nor Saliyana Jumali Jumali, Nor Saliyana Malaysia Animal biochemistry In this study, Zopfiellamide A was chosen as a target molecule due to its unique structure and its pharmacological importance. The synthetic strategy moving towards the synthesis of Zopfiellamide A was divided accordingly based on the C-5 and C-3 substitution groups. The first approached was focused on the insertion of C-5 substituents of Zopfiellamide A which is the construction of the quaternary carbon bearing the hydroxyl, isopropyl and carboxylic acid linked via the methylene group at C-5 position of the pyrrolidinone ring. Therefore, the C-3 position of the pyrrolidinone ring was protected by a methyl group. Methyl acetoacetate was dialkylated, brominated and cyclised with methylamine to form the required lactam skeleton. The synthesis of C-5 substituents involved olefination, Michael addition, alkylation and mono-decarboxylation to give decarboxylated product 30, which is closest to the target molecule 12. There were two more steps left, which are α-hydroxylation and hydrolysis of ester. The overall yield of reaction was about 30%. Meanwhile, the C-acylation on C-3 was done by preparing the studied template of pyrrolidine-2,4-dione template 38, via condensation, dieckmann cyclisation and decarboxylation reaction… Institute of Graduate Studies, UiTM 2016 Book Section PeerReviewed text en http://ir.uitm.edu.my/id/eprint/20026/1/ABS_NOR%20SALIYANA%20JUMALI%20TDRA%20VOL%2010%20IGS%2016.pdf Jumali, Nor Saliyana (2016) Synthetic studies towards the total synthesis of Zopfiellamide A / Nor Saliyana Jumali. In: The Doctoral Research Abstracts. IGS Biannual Publication, 10 (10). Institute of Graduate Studies, UiTM, Shah Alam.
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
topic Malaysia
Animal biochemistry
spellingShingle Malaysia
Animal biochemistry
Jumali, Nor Saliyana
Synthetic studies towards the total synthesis of Zopfiellamide A / Nor Saliyana Jumali
description In this study, Zopfiellamide A was chosen as a target molecule due to its unique structure and its pharmacological importance. The synthetic strategy moving towards the synthesis of Zopfiellamide A was divided accordingly based on the C-5 and C-3 substitution groups. The first approached was focused on the insertion of C-5 substituents of Zopfiellamide A which is the construction of the quaternary carbon bearing the hydroxyl, isopropyl and carboxylic acid linked via the methylene group at C-5 position of the pyrrolidinone ring. Therefore, the C-3 position of the pyrrolidinone ring was protected by a methyl group. Methyl acetoacetate was dialkylated, brominated and cyclised with methylamine to form the required lactam skeleton. The synthesis of C-5 substituents involved olefination, Michael addition, alkylation and mono-decarboxylation to give decarboxylated product 30, which is closest to the target molecule 12. There were two more steps left, which are α-hydroxylation and hydrolysis of ester. The overall yield of reaction was about 30%. Meanwhile, the C-acylation on C-3 was done by preparing the studied template of pyrrolidine-2,4-dione template 38, via condensation, dieckmann cyclisation and decarboxylation reaction…
format Book Section
author Jumali, Nor Saliyana
author_facet Jumali, Nor Saliyana
author_sort Jumali, Nor Saliyana
title Synthetic studies towards the total synthesis of Zopfiellamide A / Nor Saliyana Jumali
title_short Synthetic studies towards the total synthesis of Zopfiellamide A / Nor Saliyana Jumali
title_full Synthetic studies towards the total synthesis of Zopfiellamide A / Nor Saliyana Jumali
title_fullStr Synthetic studies towards the total synthesis of Zopfiellamide A / Nor Saliyana Jumali
title_full_unstemmed Synthetic studies towards the total synthesis of Zopfiellamide A / Nor Saliyana Jumali
title_sort synthetic studies towards the total synthesis of zopfiellamide a / nor saliyana jumali
publisher Institute of Graduate Studies, UiTM
publishDate 2016
url http://ir.uitm.edu.my/id/eprint/20026/1/ABS_NOR%20SALIYANA%20JUMALI%20TDRA%20VOL%2010%20IGS%2016.pdf
http://ir.uitm.edu.my/id/eprint/20026/
_version_ 1685649291616452608
score 13.211869

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