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

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.

Abstract

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…

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Metadata

Item Type: Book Section
Creators:
CreatorsID Num.
Jumali, Nor SaliyanaUNSPECIFIED
Subjects: L Education > LB Theory and practice of education > Higher Education > Dissertations, Academic. Preparation of theses > Malaysia
Q Science > QP Physiology > Animal biochemistry
Divisions: Institut Pengajian Siswazah (IPSis) : Institute of Graduate Studies (IGS)
Series Name: IGS Biannual Publication
Volume: 10
Number: 10
Item ID: 20026
Uncontrolled Keywords: Abstract; Abstract of thesis; Newsletter; Research information; Doctoral graduates; IPSis; IGS; UiTM;
URI: http://ir.uitm.edu.my/id/eprint/20026

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