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. 2023 Mar 22;12(3):628. doi: 10.3390/antibiotics12030628

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© 2023 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).

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Scheme 7 — Synthesis of A–33853 antibiotic (113). Reagents and conditions: (a) CDI, THF, reflux, 18 h, 60%; (b) POCl₃, xylene, 140 °C, 3 h, 58%; (c) MeOH, 40 °C, 12 h; (d) DDQ, CH₂Cl₂, r.t, 12 h, 37%; (e) Pd/C, H₂, MeOH, r.t, 12 h, 80%; (f) BnBr, Ag₂O, CH₂Cl₂/DMSO (1:1), r.t, 12 h, 70%; (g) LiOH, THF/ H₂O/MeOH (3:1:1), r.t, 12 h, 94%; (h) (COCl)₂, r.t, 3 h; (i) pyridine, DMAP (cat.), CH₂Cl₂, r.t, 12 h, 34%; and (j) excess BBr3, CH₂Cl₂, −78 °C to r.t, 16 h, 81%.