Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin

Kamaruddin, Nurulhuda (2017) Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin. In: The Doctoral Research Abstracts. IGS Biannual Publication, 12 (12). Institute of Graduate Studies, Shah Alam.

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Abstract

Janolusimide 19 was chosen to be the synthetic target molecule due to having a unique tripeptide structure besides showing a neurotoxin activity. Our synthetic approach towards the synthesis of janolusimide involved the construction of a core lactam system derived from L-valine using EDC.HCl followed by dimethylation using four different conditions. Dimethylation at C-3 position of 133 affords (5S)-3,3- dimethyl-5-isopropylpyrrolidine-2,4-dione 26 in 72% yield using TBAF as a phase transfer catalyst. In this dimethylation step, a characteristic of ambident anion also can be observed. Multiple positions of alkylation had occurred due to enolate’s ambident character of which C,O-alkylated and O-alkylated side products were observed. While the effort to synthesize the dipeptide chain was carried out using aldol reaction, N-alkylation of 26 and N-acylation of a template, 2-pyrrolidinone 139 and lactam 26 with several electrophiles. Four general protocols (Method A-D) to N-acylate 2-pyrrolidinone and lactam 26 were examined..

Item Type: Book Section
Creators:
CreatorsEmail
Kamaruddin, NurulhudaUNSPECIFIED
Subjects: Q Science > QD Chemistry > Analytical chemistry
Divisions: Institut Pengajian Siswazah (IPSis) : Institute of Graduate Studies (IGS)
Series Name: IGS Biannual Publication
Volume: 12
Number: 12
Item ID: 18952
Uncontrolled Keywords: Abstract; Abstract of Thesis; Newsletter; Research information; Doctoral graduates; IPSis; IGS; UiTM; Janolusimide
Last Modified: 22 Feb 2018 01:37
Depositing User: Admin Pendigitan 2 PTAR
URI: http://ir.uitm.edu.my/id/eprint/18952

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