Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya

In this study (-)-codonopsinine was chosen as the synthetic target molecule due to its unique trans /?e«tasubstituted pyrrolidine structure as well as remarkable antibiotic and hypotensive activity. The synthetic approach towards the total synthesis of codonopsinine requires an appropriate diketo py...

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Main Author:	Mohammat @ M Yahya, Mohd Fazli
Format:	Thesis
Language:	English
Published:	2010
Subjects:	QD Chemistry
Online Access:	https://ir.uitm.edu.my/id/eprint/5187/2/5187.pdf
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id	my-uitm-ir.5187
record_format	uketd_dc
spelling	my-uitm-ir.51872023-08-11T03:01:49Z Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya 2010 Mohammat @ M Yahya, Mohd Fazli QD Chemistry In this study (-)-codonopsinine was chosen as the synthetic target molecule due to its unique trans /?e«tasubstituted pyrrolidine structure as well as remarkable antibiotic and hypotensive activity. The synthetic approach towards the total synthesis of codonopsinine requires an appropriate diketo pyrrolidinone ring template, formed by Dieckmann cyclisation of an intermediate diester which provided the p,(3-diketo pyrrolidinone or through condensation with ring closure via multicomponent reactions to yield different (3,y-diketo ring template. Performing series of successive functional groups modification on both ring templates, which include demethoxycarbonylation, keto reduction, O-protection and P-elimination, successfully furnished over 20 pyrrolidine type compounds- in moderate to good yields. In this study, an important intermediate of olefin, 67 was successfully synthesised in 9 steps with an overall yield of 18%. Nevertheless, a different intermediate of acyloins, 82 with completed JV-Me installation in the ring was also achieved in 3 steps (with an overall yield of 18%) via the multicomponent reactions. Biological studies conducted on some of the codonopsinine derivatives confirmed to exhibit from moderate to the most potent activity towards anti-MRSA and efflux pump inhibition. In brief, two novel synthetic approaches towards the total synthesis of codonopsinine were devised which offer interesting new scientific knowledge and findings. 2010 Thesis https://ir.uitm.edu.my/id/eprint/5187/ https://ir.uitm.edu.my/id/eprint/5187/2/5187.pdf text en public phd doctoral Universiti Teknologi MARA Faculty of Applied Sciences Hamzah, Ahmad Sazali
institution	Universiti Teknologi MARA
collection	UiTM Institutional Repository
language	English
advisor	Hamzah, Ahmad Sazali
topic	QD Chemistry
spellingShingle	QD Chemistry Mohammat @ M Yahya, Mohd Fazli Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya
description	In this study (-)-codonopsinine was chosen as the synthetic target molecule due to its unique trans /?e«tasubstituted pyrrolidine structure as well as remarkable antibiotic and hypotensive activity. The synthetic approach towards the total synthesis of codonopsinine requires an appropriate diketo pyrrolidinone ring template, formed by Dieckmann cyclisation of an intermediate diester which provided the p,(3-diketo pyrrolidinone or through condensation with ring closure via multicomponent reactions to yield different (3,y-diketo ring template. Performing series of successive functional groups modification on both ring templates, which include demethoxycarbonylation, keto reduction, O-protection and P-elimination, successfully furnished over 20 pyrrolidine type compounds- in moderate to good yields. In this study, an important intermediate of olefin, 67 was successfully synthesised in 9 steps with an overall yield of 18%. Nevertheless, a different intermediate of acyloins, 82 with completed JV-Me installation in the ring was also achieved in 3 steps (with an overall yield of 18%) via the multicomponent reactions. Biological studies conducted on some of the codonopsinine derivatives confirmed to exhibit from moderate to the most potent activity towards anti-MRSA and efflux pump inhibition. In brief, two novel synthetic approaches towards the total synthesis of codonopsinine were devised which offer interesting new scientific knowledge and findings.
format	Thesis
qualification_name	Doctor of Philosophy (PhD.)
qualification_level	Doctorate
author	Mohammat @ M Yahya, Mohd Fazli
author_facet	Mohammat @ M Yahya, Mohd Fazli
author_sort	Mohammat @ M Yahya, Mohd Fazli
title	Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya
title_short	Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya
title_full	Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya
title_fullStr	Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya
title_full_unstemmed	Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya
title_sort	synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / mohd fazli mohammat @ m yahya
granting_institution	Universiti Teknologi MARA
granting_department	Faculty of Applied Sciences
publishDate	2010
url	https://ir.uitm.edu.my/id/eprint/5187/2/5187.pdf
_version_	1783733117357391872

Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya

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