Stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid
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 Authors: | , , |
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| Format: | Article |
| Language: | English |
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ARKAT USA Inc
2003
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| Online Access: | http://irep.iium.edu.my/24437/ http://irep.iium.edu.my/24437/1/Stereoselective_preparation_of_related_derivatives_of_ricinoleic_and_13S_HODE.pdf |
| _version_ | 1848779298899492864 |
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| author | Omar, Muhammad Nor Hamilton, Richard J Moynihan, Humphrey A |
| author_facet | Omar, Muhammad Nor Hamilton, Richard J Moynihan, Humphrey A |
| 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 | 2025-11-14T15:15:34Z |
| format | Article |
| id | iium-24437 |
| institution | International Islamic University Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T15:15:34Z |
| publishDate | 2003 |
| publisher | ARKAT USA Inc |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | iium-244372013-03-01T01:08:23Z http://irep.iium.edu.my/24437/ Stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid Omar, Muhammad Nor Hamilton, Richard J Moynihan, Humphrey A QD Chemistry 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. ARKAT USA Inc 2003-05 Article PeerReviewed application/pdf en http://irep.iium.edu.my/24437/1/Stereoselective_preparation_of_related_derivatives_of_ricinoleic_and_13S_HODE.pdf Omar, Muhammad Nor and Hamilton, Richard J and Moynihan, Humphrey A (2003) Stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid. ARKIVOC, 2003 (vii). pp. 190-199. ISSN 1551-7012 http://www.arkat-usa.org/about-arkat-usa/ |
| spellingShingle | QD Chemistry Omar, Muhammad Nor Hamilton, Richard J Moynihan, Humphrey A Stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid |
| title | Stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid |
| title_full | Stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid |
| title_fullStr | Stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid |
| title_full_unstemmed | Stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid |
| title_short | Stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid |
| title_sort | stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(s)-hydroxyoctadeca-9(z),11(e)-dienoic acid |
| topic | QD Chemistry |
| url | http://irep.iium.edu.my/24437/ http://irep.iium.edu.my/24437/ http://irep.iium.edu.my/24437/1/Stereoselective_preparation_of_related_derivatives_of_ricinoleic_and_13S_HODE.pdf |