Chemoenzymatic and biotransformation approaches for pharmaceutical applications
Methyl ricinoleate 4 and methyl 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoate 7 were subjected to epoxidation using mCPBA, or tert-butyl hydroperoxide in the presence of vanadyl acetylacetonate or titanium (IV) isopropoxide with D-(-)- or L-(+)-diisopropyl tartrate. Epoxidations using mCPBA gave equal q...
| Main Author: | |
|---|---|
| Format: | Proceeding Paper |
| Language: | English English English English |
| Published: |
2009
|
| Subjects: | |
| Online Access: | http://irep.iium.edu.my/17951/ http://irep.iium.edu.my/17951/1/Planery_lecture_NSFT09.pdf http://irep.iium.edu.my/17951/2/Fermentation_technology.PDF http://irep.iium.edu.my/17951/3/NSFT_2009_planery.PDF http://irep.iium.edu.my/17951/4/NSFT_Plenary1.pdf |
| _version_ | 1848778129809604608 |
|---|---|
| author | Omar, Muhammad Nor |
| author_facet | Omar, Muhammad Nor |
| author_sort | Omar, Muhammad Nor |
| building | IIUM Repository |
| collection | Online Access |
| description | Methyl ricinoleate 4 and methyl 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoate 7 were subjected to epoxidation using mCPBA, or tert-butyl hydroperoxide in the presence of vanadyl acetylacetonate or titanium (IV) isopropoxide with D-(-)- or L-(+)-diisopropyl tartrate. Epoxidations using mCPBA gave equal quantities of the disatereoisomeric epoxides 5/6 and 8/9 from 4 and 7 respectively. Other methods gave preferentially epoxides 5 or 8, except for treatment of 7 with tert-butyl hydroperoxide in the presence of titanium (IV) isopropoxide and L-(+)-diisopropyl tartrate which gave preferentially epoxide 9. Hydroxy-derivative 4, 7, 5, 6, 8 and 9 were converted into the fluoro-derivatives 16 - 21 by trimethylsilylation and treament with diethylaminosulphur trifluoride. Epoxides 6 and 9 were converted into 2-oxazolines 22 and 23 respectively by reaction with acetamide. |
| first_indexed | 2025-11-14T14:56:59Z |
| format | Proceeding Paper |
| id | iium-17951 |
| institution | International Islamic University Malaysia |
| institution_category | Local University |
| language | English English English English |
| last_indexed | 2025-11-14T14:56:59Z |
| publishDate | 2009 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | iium-179512012-03-08T01:56:08Z http://irep.iium.edu.my/17951/ Chemoenzymatic and biotransformation approaches for pharmaceutical applications Omar, Muhammad Nor Q Science (General) Methyl ricinoleate 4 and methyl 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoate 7 were subjected to epoxidation using mCPBA, or tert-butyl hydroperoxide in the presence of vanadyl acetylacetonate or titanium (IV) isopropoxide with D-(-)- or L-(+)-diisopropyl tartrate. Epoxidations using mCPBA gave equal quantities of the disatereoisomeric epoxides 5/6 and 8/9 from 4 and 7 respectively. Other methods gave preferentially epoxides 5 or 8, except for treatment of 7 with tert-butyl hydroperoxide in the presence of titanium (IV) isopropoxide and L-(+)-diisopropyl tartrate which gave preferentially epoxide 9. Hydroxy-derivative 4, 7, 5, 6, 8 and 9 were converted into the fluoro-derivatives 16 - 21 by trimethylsilylation and treament with diethylaminosulphur trifluoride. Epoxides 6 and 9 were converted into 2-oxazolines 22 and 23 respectively by reaction with acetamide. 2009 Proceeding Paper NonPeerReviewed application/pdf en http://irep.iium.edu.my/17951/1/Planery_lecture_NSFT09.pdf application/pdf en http://irep.iium.edu.my/17951/2/Fermentation_technology.PDF application/pdf en http://irep.iium.edu.my/17951/3/NSFT_2009_planery.PDF application/pdf en http://irep.iium.edu.my/17951/4/NSFT_Plenary1.pdf Omar, Muhammad Nor (2009) Chemoenzymatic and biotransformation approaches for pharmaceutical applications. In: 2nd National Symposium on Fermentation Technology (NSFT 2009), 14-15 December 2009, MITC Ayer Keroh Malacca. (Unpublished) |
| spellingShingle | Q Science (General) Omar, Muhammad Nor Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
| title | Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
| title_full | Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
| title_fullStr | Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
| title_full_unstemmed | Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
| title_short | Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
| title_sort | chemoenzymatic and biotransformation approaches for pharmaceutical applications |
| topic | Q Science (General) |
| url | http://irep.iium.edu.my/17951/ http://irep.iium.edu.my/17951/1/Planery_lecture_NSFT09.pdf http://irep.iium.edu.my/17951/2/Fermentation_technology.PDF http://irep.iium.edu.my/17951/3/NSFT_2009_planery.PDF http://irep.iium.edu.my/17951/4/NSFT_Plenary1.pdf |