|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|
|Date Published||2021 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 Journal||J Org Chem|