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Synthesis 1987; 1987(7): 607-611
DOI: 10.1055/s-1987-28021
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Synthons for Polyketides: An Improved Synthesis of Methyl 3,3-Dialkoxy-2-methylpropanoates

Robert D. Walkup* , Nihal U. Obeyesekere
  • *Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409, U.S.A.
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Publication Date:
20 August 2002 (online)

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A versatile conversion of methyl methacrylate to methyl 3,3-dialkoxy-2-methylpropanoates proceeds via bromination, then treatment with excess sodium methoxide to yield methyl 3,3-dimethoxy-2-methylpropanoate, which can be transacetalized by treatment with alcohols under acid catalysis to yield the title compounds. Stereoselective chain-extension reactions of these compounds by aldol additions to the aldehydes derived from the ester group (C-1), or by titanium(IV)-mediated allylsilane additions to the acetal carbon (C-3), are examples of the potential utility of methyl 3,3-dialkoxy-2-methylpropanoates to natural products, syntheses.

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