TY - JOUR
T1 - Synthesis of a mevinic acid lactone precursor
AU - Mash, Eugene A.
AU - Arterburn, Jeffrey B.
AU - Nimkar, Sandeep K.
N1 - Funding Information:
JBA thanks the Division of Organic Chemistry of the American Chemical Society for a Graduate Fellowship sponsored by Smith-Kline and French Laboratories. Partial support of this research by the Elsa U. Pardee Foundation and by Research Corporation is gratefully acknowledged.
PY - 1992/6/1
Y1 - 1992/6/1
N2 - 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.
AB - 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.
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U2 - 10.1080/07328309208017803
DO - 10.1080/07328309208017803
M3 - Article
AN - SCOPUS:0008515715
SN - 0732-8303
VL - 11
SP - 415
EP - 424
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
IS - 4
ER -