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

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...

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Main Authors: Omar, Muhammad Nor, Hamilton, Richard J, Moynihan, Humphrey A
Format: Article
Language:English
Published: ARKAT USA Inc 2003
Subjects:
QD Chemistry
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
id iium-24437
recordtype eprints
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/
repository_type Digital Repository
institution_category Local University
institution International Islamic University Malaysia
building IIUM Repository
collection Online Access
language English
topic QD Chemistry
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
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.
format Article
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
title 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_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_sort stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(s)-hydroxyoctadeca-9(z),11(e)-dienoic acid
publisher ARKAT USA Inc
publishDate 2003
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
first_indexed 2023-09-18T20:36:38Z
last_indexed 2023-09-18T20:36:38Z
_version_ 1777409089542815744

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