Synthesis of a mevinic acid lactone precursor

Eugene A. Mash, Jeffrey B. Arterburn, Sandeep K. Nimkar

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Abstract

A synthesis of (S)-l-phenyl-2-(turt-butyldiphenyIsilyloxy)ethyl (2R, 4R, 6S)-4-tert- butyldiphenylsilyloxy-6-hydroxymethyl-3, 4, 5, 6-tetrahydro-2H-pyran-2-yl ether, a potentially valuable precursor to the mevinic acid lactone, is described. The synthesis begins with commercially available racemic sodio-3, 4-dihydro-2H-pyran-2-carboxylate and utilizes a chromatographic resolution of diastereomeric (S)-methyl mandelyl pyranosides and a directed epoxidation. The overall yield, 21% over 10 steps, is competitive with routes from carbohydrates to comparable mevinic acid lactone precursors.

Original languageEnglish (US)
Pages (from-to)415-424
Number of pages10
JournalJournal of Carbohydrate Chemistry
Volume11
Issue number4
DOIs
StatePublished - Jun 1 1992

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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