Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthetic Studies of Rifamycins. VII. A Facile Synthesis of the Aromatic Chromophore of Rifamycin S through a Rifamycin W Aromatic Segment
Masaya NakataShigeru WadaKuniaki TatsutaMitsuhiro Kinoshita
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1985 Volume 58 Issue 6 Pages 1801-1806

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Abstract

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

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