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Catalytic Asymmetric Synthesis of Phthioceranic Acid, a Heptamethyl-Branched Acid from Mycobacterium tuberculosis

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    Catalytic Asymmetric Synthesis of Phthioceranic Acid, a Heptamethyl-Branched Acid from Mycobacterium tuberculosis
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    Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborg 4, 9747AG, Groningen, The Netherlands
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    Organic Letters

    Cite this: Org. Lett. 2007, 9, 16, 3013–3015
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    https://doi.org/10.1021/ol071078o
    Published July 14, 2007
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    Abstract

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    The first total synthesis of phthioceranic acid (1) has been achieved by an iterative catalytic asymmetric 1,4-addition protocol. This method provides a robust and high-yielding route for the preparation of 1,3-oligomethyl (deoxypropionate) arrays. After the desired number of methyl groups has been introduced, these arrays can be further functionalized at both ends to polymethyl-substituted lipids such as phthioceranic acid, a heptamethyl-branched fatty acid from the virulence factor Sulfolipid-I (2), found in Mycobacterium tuberculosis.

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    Cite this: Org. Lett. 2007, 9, 16, 3013–3015
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    https://doi.org/10.1021/ol071078o
    Published July 14, 2007
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