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  • Title: Synthesis and antioxidant properties of an unnatural plasmalogen analogue bearing a trans O-vinyl ether linkage.
    Author: Lankalapalli RS, Eckelkamp JT, Sircar D, Ford DA, Subbaiah PV, Bittman R.
    Journal: Org Lett; 2009 Jul 02; 11(13):2784-7. PubMed ID: 19499908.
    Abstract:
    To assess the antioxidant behavior of trans-1, we first synthesized trans-allyl ether 4 by opening an (S)-glycidol derivative with an (E)-alk-2-en-ol, and then produced the unnatural E-enol ether 1 by a stereoselective iridium(I)-catalyzed olefin isomerization. Natural cis-1 was preferentially degraded by HOCl and was more protective than trans-1 against lipid peroxidation induced by a free-radical initiator, demonstrating that the geometry of the 1'-alkenyloxy bond participates in the antioxidant defensive role of 1.
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