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. Author manuscript; available in PMC: 2020 Feb 20.
Published in final edited form as: J Am Chem Soc. 2019 Feb 11;141(7):3083–3099. doi: 10.1021/jacs.8b12247

Scheme 3.

Scheme 3.

Successful Oxidation of C14a

aReagents and conditions: (a) PhI(OAc)2 (3.0 equiv), I2 (1.0 equiv), cyclohexane, hν (visible), 1.5 h, 73%; (b) Me3OBF4 (1.5 equiv), proton sponge (1.5 equiv), DCM, 55 °C, 12 h, 97%; (c) NaIO4 (5.0 equiv), RuCl3•xH2O (0.1 equiv), CCl4:MeCN:H2O (3:3:4), 1 h, 72%; d) CuBr2 (3.0 equiv), t-BuOH (3.0 equiv), diglyme, 150 °C, 12 h; (e) KOH (1.0 equiv), KOt-Bu (3.0 equiv), DMSO, 14 h, 45% (two steps), d.r. = 4:1; (f) NaH (5.0 equiv), TBSCl (4.0 equiv), THF, 65 °C, 8 h then add 3.0 M HCl (16 equiv), 65 °C, 16 h, 88%.