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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| Format: | Thesis |
| Language: | English |
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2010
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| Online Access: | https://ir.uitm.edu.my/id/eprint/5187/ |
| _version_ | 1848802774496575488 |
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| author | Mohammat @ M Yahya, Mohd Fazli |
| author_facet | Mohammat @ M Yahya, Mohd Fazli |
| author_sort | Mohammat @ M Yahya, Mohd Fazli |
| building | UiTM Institutional Repository |
| collection | Online Access |
| 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. |
| first_indexed | 2025-11-14T21:28:42Z |
| format | Thesis |
| id | uitm-5187 |
| institution | Universiti Teknologi MARA |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:28:42Z |
| publishDate | 2010 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | uitm-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 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. (2010) PhD thesis, thesis, Universiti Teknologi MARA. |
| 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 |
| title | 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_short | 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 |
| topic | QD Chemistry |
| url | https://ir.uitm.edu.my/id/eprint/5187/ |