Synthesis of Methyl Axenoside and Methyl 3-epi-Axenoside via Ate-Mediated Allylic Substitution (AMAS)

An ate-mediated allylic substitution (AMAS) of vinylboronates is utilized in the divergent syntheses of the sugars methyl axenoside and methyl 3- epi -axenoside. Other key steps of the synthesis involve the dihydroxylation of the resulting allylic alcohol and selective oxidation of the resultant diol. Benefits of this methodology are also discussed.