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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
https://ir.uitm.edu.my/id/eprint/5187/
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spelling my.uitm.ir.51872023-08-11T03:01:49Z https://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 https://ir.uitm.edu.my/id/eprint/5187/2/5187.pdf Synthetic studies towards the total synthesis of (-)-codonopsinine, an anti-hypertensive compound from codonopsis clematidea / Mohd Fazli Mohammat @ M Yahya. (2010) PhD thesis, thesis, Universiti Teknologi MARA.
institution Universiti Teknologi Mara
building Tun Abdul Razak Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Mara
content_source UiTM Institutional Repository
url_provider http://ir.uitm.edu.my/
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 https://ir.uitm.edu.my/id/eprint/5187/2/5187.pdf
https://ir.uitm.edu.my/id/eprint/5187/
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score 13.211869

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