PURPOSE: To obtain an azoxy compound useful as an intermediate for maniwamycin having strong antibacterial activity in high yield by introducing an N-oxide group by an easy and selective oxidation reaction of azo group using an easily available reagent.
CONSTITUTION: An α, β-unsaturated azoxy compound of formula 1 can be produced by reacting a compound of formula 2 (R is alkyl, alkenyl, alkynyl, aryl or aralkyl) with a compound of formula 3 (A is amino-protecting group) to obtain a compound of formula 4, reducing the carbonyl group and protecting the OH of the compound, activating the amino group of the obtained compound of formula 5 (B is OH-protecting group), reacting with a compound of formula 6 to get a compound of formula 7, subjecting the compound to the protection of OH group, the elimination of the protecting group B, the elimination of the amino-protecting group and the oxidation of hydrazine to obtain a compound of formula 8 (B' is OH-protecting group), selectively oxidizing the OH-side amino group of the compound and finally dehydrating the obtained compound of formula 9 and eliminating the OH-protecting group.
YAMAMOTO KATSUHIRO
OKUNO YUKIHIRO
TAKAHASHI YOSHIO
IDEUSHI TAKEO
SHIRATO SHOZO
NAKADA MASAYA
TATSUTA KUNIAKI
