Synthesis of 3-methyl-5-nitrobenzyl -diketoester as a derivative of pachydermin a tetramic acid from Chamonixia pachydermis

Mohd Fazli Mohammat, . and Zurina Shaameri, . and Noorhana Hussain, . and Noor Hidayah Pungot, . and Ahmad Sazali Hamzah, . Synthesis of 3-methyl-5-nitrobenzyl -diketoester as a derivative of pachydermin a tetramic acid from Chamonixia pachydermis. pp. 1-7. ISSN 1823-8556

Pachydermin an oxylated tetramic acid with 3-chloro-4-hydroxyphenyl substituent was isolated from Chamonixia pachydermis plant a basidiomycete of New Zealand. Its degradation product exhibits antibacterial activity against Bacillus subtilis and the derivatives of pachydermin are anticipated to have similar potentials. In this work a novel approach to synthesize 3-methyl-5-nitrobenzyl -diketoester was developed as a derivative of the natural product pachydermin. The synthetic route began with the synthesis of N-benzylated -diketoester as the key structural moiety from glycine methyl ester as the starting material. Subsequently oxalyl subunit was inserted as well as other acyl/alkyl subunits at C-3 position of the -diketoester ring via acylation/alkylation reactions leading to the required intermediates towards pachydermin and its derivatives. Alkene functionalities at C-5 position could then be introduced using different alkyl or aryl aldehydes with the aid of different bases which included diisopropylamine NaH Et3 N K2 CO3 as well as ionic liquids. Insertions of methyl and 4-nitrobenzylidene functionalities at C3- and C5-positions respectively were highlighted for the synthesis of the target derivative. Selective decarboxylation ester hydrolysis and N-benzyl deprotection should lead to the required target compound and derivatives. All the synthesized compounds were confirmed by the mass spectroscopy (MS) and nuclear magnetic resonance (NMR) spectroscopy.

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Abstract

Pachydermin an oxylated tetramic acid with 3-chloro-4-hydroxyphenyl substituent was isolated from Chamonixia pachydermis plant a basidiomycete of New Zealand. Its degradation product exhibits antibacterial activity against Bacillus subtilis and the derivatives of pachydermin are anticipated to have similar potentials. In this work a novel approach to synthesize 3-methyl-5-nitrobenzyl -diketoester was developed as a derivative of the natural product pachydermin. The synthetic route began with the synthesis of N-benzylated -diketoester as the key structural moiety from glycine methyl ester as the starting material. Subsequently oxalyl subunit was inserted as well as other acyl/alkyl subunits at C-3 position of the -diketoester ring via acylation/alkylation reactions leading to the required intermediates towards pachydermin and its derivatives. Alkene functionalities at C-5 position could then be introduced using different alkyl or aryl aldehydes with the aid of different bases which included diisopropylamine NaH Et3 N K2 CO3 as well as ionic liquids. Insertions of methyl and 4-nitrobenzylidene functionalities at C3- and C5-positions respectively were highlighted for the synthesis of the target derivative. Selective decarboxylation ester hydrolysis and N-benzyl deprotection should lead to the required target compound and derivatives. All the synthesized compounds were confirmed by the mass spectroscopy (MS) and nuclear magnetic resonance (NMR) spectroscopy.

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Item Type:	Article
AGROVOC Term:	Basidiomycotina
AGROVOC Term:	Bacillus subtilis
AGROVOC Term:	Antibacterial properties
AGROVOC Term:	Chemical composition
AGROVOC Term:	Degradation
AGROVOC Term:	Chemical synthesis
AGROVOC Term:	Chemical reactions
AGROVOC Term:	Aldehydes
AGROVOC Term:	Esters
AGROVOC Term:	Mass spectroscopy
Depositing User:	Ms. Suzila Mohamad Kasim
Last Modified:	24 Apr 2025 06:28
URI:	http://webagris.upm.edu.my/id/eprint/24193

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