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Synthesis of Plm inhibitor (S,R)–4g. Reagents and conditions: a) aqueous 1 N NaOH (3 equiv), MeOH, 40 °C, 18 h b) Pd(dppf)Cl2xCH2Cl2 (10 mol%), NEt3 (2.2 equiv), CO (70 psi), MeOH, 100 °C, 18 h c) General procedure B: (n-Pr)2NH (2.2 equiv), HBTU (2 equiv), NEt3 (4 equiv), DMF, rt, 2 h d) General procedure C: aqueous 1 M NaOH (1.5 equiv), MeOH, 50 °C, 18 h e) General procedure D: amino alcohol (R,S)–11 (1.0 equiv), HBTU (1.0 equiv), NEt3 (4 equiv), DMF, rt, 16 h.
