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

M S Lie Ken Jie; J Mustafa; M K Pasha

doi:10.1007/s11745-998-0291-x

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

Lipids. 1998 Sep;33(9):941-5. doi: 10.1007/s11745-998-0291-x.

Authors

M S Lie Ken Jie¹, J Mustafa, M K Pasha

Affiliation

¹ Department of Chemistry, University of Hong Kong, Hong Kong. hrsclkj@hkucc.hku.hk

PMID: 9778142
DOI: 10.1007/s11745-998-0291-x

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Biochemistry / methods*
Fatty Acids / chemistry*
Magnetic Resonance Spectroscopy
Oxidation-Reduction
Ultrasonography
Zinc / chemistry*

Substances

Alkynes
Fatty Acids
methyl 8-hydroxy-11-octadecen-9-ynoate
Zinc