Abstract
A reaction of epoxy alcohols (anti and/or syn isomers) derived from (E)-TMS-CH=CHCH(OH)R with TMS-C≡CLi in THF/HMPA stereoselectively afforded (E)-TMS-C≡C-CH=CHCH(OH)R. The (E) stereochemistry was independent of the anti/syn stereochemistry, but the syn isomers showed higher reactivity than the anti isomers. The reaction was applied to the synthesis of (18R)- and (18S)-HEPE.
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