An efficient ultrasound‐assisted zinc reduction of fatty esters containing conjugated enynol and conjugated enynone systems

Reduction of methyl 8‐hydroxy‐11‐E/Z‐octadecen‐9‐ynoate (1) with zinc in either aqueous n‐propanol or water under concomitant ultrasound irradiation furnished a mixture of methyl 8‐hydroxy‐9Z,11E‐octadecadienoate (3a) and methyl 8‐hydroxy‐9Z, 11Z‐octadecadienoate (3b) (96% yield). Reduction of methy...

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Bibliographic Details
Published in:Lipids 1998-09, Vol.33 (9), p.941-945
Main Authors: Lie Ken Jie, Marcel S. F., Mustafa, Jamal, Pasha, Mohammed Khysar
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Biochemistry - methods
Esters
Fatty Acids - chemistry
Irradiation
Magnetic Resonance Spectroscopy
Oxidation-Reduction
Ultrasonography
Zinc - chemistry
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Summary:Reduction of methyl 8‐hydroxy‐11‐E/Z‐octadecen‐9‐ynoate (1) with zinc in either aqueous n‐propanol or water under concomitant ultrasound irradiation furnished a mixture of methyl 8‐hydroxy‐9Z,11E‐octadecadienoate (3a) and methyl 8‐hydroxy‐9Z, 11Z‐octadecadienoate (3b) (96% yield). Reduction of methyl 8‐oxo‐11‐E/Z‐octadecen‐9‐ynoate (2) under similar conditions gave methyl 8‐oxo‐10‐Z‐octadecenoate exclusively (4, 70%). The latter compound was epoxidized and converted to a C18 furanoid fatty ester (6, methyl 8,11‐epoxy‐8,10‐octadecadienoate) in 70% yield.
ISSN:0024-4201
1558-9307
DOI:10.1007/s11745-998-0291-x