Synthetic studies of rifamycins. VII. A facile synthesis of the aromatic chromophore of rifamycin S through a rifamycin W aromatic segment

Article abstract of DOI:10.1246/bcsj.58.1801

The intact aromatic chromophore of rifamycin S, 7-amino-2,5-dihydroxy-2,4-dimethyl-naphtho[2,l-b]furan-1,6,9-(2H)-trion e, was synthesized through the rifamycin W aromatic segment, 1-[5,8-dimethoxy-2,4-bis-(methoxymethoxy)-3-methyl-6-nitro-l-naphthyl]- l-propanone which was prepared in 9 steps and 29.6% overall yield from 2,6-bis(benzyloxy)-3,5-dibromotoluene and furan.