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

Patrick H Dussault, In Quen Lee

Research output: Contribution to journalArticle

20 Citations (Scopus)

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

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Acids
Regioselectivity
Lipoxygenase
Aldehydes
Hydrogen Peroxide
Esters
Fats
Substrates
metsulfuron methyl

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A Chemoenzymatic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE. / Dussault, Patrick H; Lee, In Quen.

In: Journal of Organic Chemistry, Vol. 60, No. 1, 01.01.1995, p. 218-226.

Research output: Contribution to journalArticle

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