4.6 Article

Total synthesis of C-19 lipid diols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 7, Pages 2198-2208

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob00754d

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Funding

  1. Australian Postgraduate Award

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The total synthesis of the C-19 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.

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