Alkanediazoates. Part XIII. Synthesis of azoxyalkanes: L-dihydroelaiomycin [4-methoxy-3-(octyl-ONN-azoxy)butan-2-ol]

Abstract

L-Threonine was converted in ten steps into potassium (2R,3R)-1-methoxy-3-tetrahydropyranyloxybutane-2-diazoate (10), which was then alkylated with n-octyl iodide. Removal of the tetrahydropyranyl group afforded L-dihydroelaiomycin in an overall yield of 8% for twelve steps. The synthetic product was compared with its D-enantiomer, prepared by reduction of natural elaiomycin over 5% rhodium–alumina.