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
Volume86
Issue11
Pagination7773-7780
Date Published2021 Jun 04
ISSN1520-6904
Abstract

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 .

DOI10.1021/acs.joc.1c00528
Alternate JournalJ Org Chem
PubMed ID34000192