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.
ASJC Scopus subject areas
- Organic Chemistry