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. 2020 Oct 16;63(21):12814–12829. doi: 10.1021/acs.jmedchem.0c01191

Scheme 1. Synthesis of Hybrid Monosaccharide Anthracyclines 24.

Scheme 1

Reagents and conditions: (a) 0.2 M aqueous (aq) HCl, 90 °C, quant.; (b) PPh3AuNTf2 (10 mol %), dichloromethane (DCM), −20 °C, 73% (>20:1 α/β); (c) (i) Pd(PPh3)4, NDMBA, DCM, (ii) HF·pyridine, pyr., 40% over two steps; (d) (i) Pd(PPh3)4, NDMBA, DCM, (ii) aq CH2O, NaBH(OAc)3, EtOH, (iii) HF·pyridine, pyr., 43% over three steps; (e) (i) aq HCl, 90 °C, (ii) TBS-Cl, imidazole, dimethylformamide (DMF), 97% over two steps.