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Issue 7, 2011
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Total synthesis of C19 lipid diols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran

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Abstract

The total synthesis of the C19 lipid diols 5 and 6, the enantiomers of the anthelmintic marine natural products 1 and 3, is described. Key steps in the divergent syntheses include a syn selective epoxidation of a homoallylic alcohol, a one-pot alkoxypalladation-carbonylation-lactonisation reaction sequence and a DMEAD promoted Mitsunobu inversion.

Graphical abstract: Total synthesis of C19 lipid diols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran

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Publication details

The article was received on 21 Sep 2010, accepted on 17 Dec 2010 and first published on 20 Dec 2010


Article type: Paper
DOI: 10.1039/C0OB00754D
Citation: Org. Biomol. Chem., 2011,9, 2198-2208
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    Total synthesis of C19 lipid diols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran

    C. L. Nesbitt and C. S. P. McErlean, Org. Biomol. Chem., 2011, 9, 2198
    DOI: 10.1039/C0OB00754D

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