TitleTotal Synthesis of Chalaniline B: An Antibiotic Aminoxanthone from Vorinostat-Treated Fungus sp. 6661.
Publication TypeJournal Article
Year of Publication2021
AuthorsKhoshbakht M, Thanaussavadate B, Zhu C, Cao Y, Zakharov LN, Loesgen S, Blakemore PR
JournalJ Org Chem
Date Published2021 Jun 04

Chalaniline B [1-anilino-2,8-dihydroxy-3-(hydroxymethyl)xanthone], an antibiotic previously isolated from vorinostat-treated sp., was prepared in 7 steps from 2-hydroxyxanthone by a route incorporating regioselective oxidative transformations (bromination at C1/C3, ketone directed Pd(II)-catalyzed hydroxylation at C8), installation of the C1-anilino moiety by a regioselective Buchwald-Hartwig amination reaction from 1,3-dibromo-2,8-dimethoxyxanthone, and late-stage hydroxymethylation at C3 using a Stille cross-coupling. Biological evaluation of deshydroxymethylchalaniline B (1-anilino-2,8-dihydroxyxanthone) revealed MIC values of 8 μg mL (25 μM) against both methicillin resistant and .

Alternate JournalJ Org Chem
PubMed ID34000192