Abstract
The naturally occurring δ-hydroxy- γ-lactone (4R,5R)-muricatacin and its nonnatural (4R,5S)-analog are synthesized. The starting achiral allylic alcohols are converted into α,β-epoxy diazomethyl ketones followed by a stereospecific irradiation reaction of these compounds to give 4-hydroxy-2-alkene esters. Using this method in a sequential manner a successive introduction of stereogenic centers is realized, resulting in enantiopure 4,5-dihydroxy-2-alkene esters. These alcohols are converted into the δ-hydroxy- γ-lactone muricatacin.
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