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Synthesis ofE,E-diene hydroperoxides via photoisomerization of protected hydroperoxides

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Lipids

Abstract

A general approach toE,E-diene hydroperoxides is described based upon photoisomerization of readily availableZ,E-diene monoperoxyketals. Protection of aZ,E-diene hydroperoxide as the 2-methoxypropyl peroxyketal is followed by iodine-mediated photoisomerization to produce a mixture enriched in theE,E isomer. After chromatographic purification, deprotection of the peroxyketal with mild acid furnishes theE,E-diene hydroperoxide.

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Abbreviations

EA:

ethyl acetate

13-HPOD:

13(S)-hydroperoxy-9Z-11E-octadecadienoic acid

15(S)-HPETE:

15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid

5(S)-HPETE:

5(S)-hydroperoxy-6E,8Z,11Z,14Z-eicosatetraenoic acid

NP-HPLC:

normal-phase high-performance liquid chromatography

NMR:

nuclear magnetic resonance

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Authors and Affiliations

  1. Department of Chemistry, University of Nebraska-Lincoln, 68588-0304, Lincoln, Nebraska

    P. H. Dussault, I. Q. Lee & C. T. Eary

Authors
  1. P. H. Dussault
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  2. I. Q. Lee
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  3. C. T. Eary
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Dussault, P.H., Lee, I.Q. & Eary, C.T. Synthesis ofE,E-diene hydroperoxides via photoisomerization of protected hydroperoxides. Lipids 30, 591–594 (1995). https://doi.org/10.1007/BF02536994

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  • DOI: https://doi.org/10.1007/BF02536994

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