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...

Full description

Bibliographic Details
Main Author:	Mohammat @ M Yahya, Mohd Fazli
Format:	Thesis
Language:	English
Published:	2010
Subjects:	QD Chemistry
Online Access:	http://ir.uitm.edu.my/id/eprint/5187/ http://ir.uitm.edu.my/id/eprint/5187/1/TP_MOHD%20FAZLI%20MOHAMMAT%20%40%20M%20YAHYA%20AS%2010_5%201.pdf

id	uitm-5187
recordtype	eprints
spelling	uitm-51872016-11-26T01:11:40Z http://ir.uitm.edu.my/id/eprint/5187/ Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya 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 NonPeerReviewed text en http://ir.uitm.edu.my/id/eprint/5187/1/TP_MOHD%20FAZLI%20MOHAMMAT%20%40%20M%20YAHYA%20AS%2010_5%201.pdf Mohammat @ M Yahya, Mohd Fazli (2010) Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya. PhD thesis, Universiti Teknologi MARA.
repository_type	Digital Repository
institution_category	Local University
institution	Universiti Teknologi MARA
building	UiTM Institutional Repository
collection	Online Access
language	English
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
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
publishDate	2010
url	http://ir.uitm.edu.my/id/eprint/5187/ http://ir.uitm.edu.my/id/eprint/5187/1/TP_MOHD%20FAZLI%20MOHAMMAT%20%40%20M%20YAHYA%20AS%2010_5%201.pdf
first_indexed	2023-09-18T22:47:02Z
last_indexed	2023-09-18T22:47:02Z
_version_	1777417293876166656

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

Similar Items