Synthesis of (4R,5R)-Muricatacin and its (4R,5S)-Analog by Sequential Use of the Photo-Induced Rearrangement of Epoxy Diazomethyl Ketones

Article abstract of DOI:10.1016/0040-4020(95)00670-4

The naturally occuring 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.