A Chemoenzymatic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE

Patrick Dussault, In Quen Lee

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

A new synthetic approach to enantiomeric ally pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.

Original languageEnglish (US)
Pages (from-to)218-226
Number of pages9
JournalJournal of Organic Chemistry
Volume60
Issue number1
DOIs
StatePublished - Jan 1 1995

ASJC Scopus subject areas

  • Organic Chemistry

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