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Synthesis of E,E-diene hydroperoxides via photoisomerization of protected hydroperoxides
P H Dussault1, I Q Lee, C T Eary
1Department of Chemistry, University of Nebraska-Lincoln 68588-0304, USA.
Lipids
|July 1, 1995
Abstract:
A general approach to E,E-diene hydroperoxides is described based upon photoisomerization of readily available Z,E-diene monoperoxyketals. Protection of a Z,E-diene hydroperoxide as the 2-methoxypropyl peroxyketal is followed by iodine-mediated photoisomerization to produce a mixture enriched in the E,E isomer. After chromatographic purification, deprotection of the peroxyketal with mild acid furnishes the E,E-diene hydroperoxide.