Stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid

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

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Abstract

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.

Item Type:	Article (Journal)
Additional Information:	5626/24437
Uncontrolled Keywords:	Oxygenated fatty acids, fluorinated fatty acids, epoxidation, 2-oxazolines
Subjects:	Q Science > QD Chemistry
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button):	Kulliyyah of Science > Department of Biotechnology
Depositing User:	Prof Dr Muhammad Nor Omar
Date Deposited:	01 Mar 2013 09:08
Last Modified:	01 Mar 2013 09:08
URI:	http://irep.iium.edu.my/id/eprint/24437

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