Title | Total Synthesis of Chalaniline B: An Antibiotic Aminoxanthone from Vorinostat-Treated Fungus sp. 6661. |
Publication Type | Journal Article |
Year of Publication | 2021 |
Authors | Khoshbakht M, Thanaussavadate B, Zhu C, Cao Y, Zakharov LN, Loesgen S, Blakemore PR |
Journal | J Org Chem |
Volume | 86 |
Issue | 11 |
Pagination | 7773-7780 |
Date Published | 2021 Jun 04 |
ISSN | 1520-6904 |
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 . |
DOI | 10.1021/acs.joc.1c00528 |
Alternate Journal | J Org Chem |
PubMed ID | 34000192 |