Unbound MEDLINE

An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala.

Abstract

Short, high yielding syntheses of both diastereomers of the naturally occurring oxylipids 1 and 2 using a combination of organocatalytic hydroxylation of an aldehyde, alkene cross metathesis, and palladium(0) catalyzed cyclization chemistry (six-step process) are reported. Furthermore, the influence of the catalyst on the cross metathesis reaction of the homoallylic 1,2-diol has been studied in detail.

Links

  • PMC Free PDF
  • Publisher Full Text

    • Authors

    Roy S, Spilling CD

    Institution

    Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121, United States.

    Source

    Organic letters 14:9 2012 May 4 pg 2230-3

    MeSH

    Alkenes
    Catalysis
    Cyclization
    Furans
    Lipids
    Molecular Structure
    Palladium
    Phaeophyta
    Stereoisomerism

    Pub Type(s)

    Journal Article
    Research Support, N.I.H., Extramural
    Research Support, Non-U.S. Gov't
    Research Support, U.S. Gov't, Non-P.H.S.

    Language

    eng

    PubMed ID

    22506757