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

Caroline L. Nesbitt; Christopher S. P. McErlean

doi:10.1039/C0OB00754D

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Total synthesis of C₁₉lipiddiols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran†‡

Caroline L. Nesbitt^a and Christopher S. P. McErlean*^a

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* Corresponding authors

^a School of Chemistry, The University of Sydney, Australia
E-mail: christopher.mcerlean@sydney.edu.au
Fax: +61 2 9351 3329
Tel: +61 2 9351 3970

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.

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Article information

DOI: https://doi.org/10.1039/C0OB00754D
Article type: Paper
Submitted: 21 Sep 2010
Accepted: 17 Dec 2010
First published: 20 Dec 2010

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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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Organic & Biomolecular Chemistry