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 |
| Published: |
ARKAT USA Inc
2003
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| Subjects: | |
| Online Access: | 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 |
| Summary: | 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. |
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