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. Author manuscript; available in PMC: 2019 Jun 14.
Published in final edited form as: J Med Chem. 2018 May 24;61(11):4946–4960. doi: 10.1021/acs.jmedchem.8b00419

Scheme 3. Analogs prepared via hydroboration-oxidation of enol triflate 2a.

Scheme 3.

aReagents and conditions: (a) BH3·THF, THF, 0 °C, 3 h, then H2O followed by NaBO3•H2O, 18 h, 0 °C to rt, 18 h, 31% (and 39% of recovered starting material); (b) diethyl(3-pyridyl)borane, Pd(PPh3)2Cl2, NaHCO3, THF, H2O, 60 °C, 20 h, 49%; (c) K2CO3, MeOH, rt, 15 h, 92%; (d) Dess–Martin periodinane, CH2Cl2, 0 °C to rt, 16 h, 89%; (e) diethyl(3-pyridyl)borane, Pd(PPh3)2Cl2, NaHCO3, THF, H2O, 60 °C, 17 h, 82%; (f) K2CO3, MeOH, rt, 17 h, 88%; (g) NH2OH•HCl, NaOAc, EtOH, H2O, rt, 17 h, 83%; (h) NH2OH•HCl, NaOAc, EtOH, H2O, rt, 24 h, 98%; (i) SOCl2, THF, 0 °C, 4 h, then H2O, 47%; (j) K2CO3, MeOH, rt, 17 h, 100%.