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. Author manuscript; available in PMC: 2021 Nov 30.
Published in final edited form as: J Med Chem. 2021 Aug 20;64(17):12506–12524. doi: 10.1021/acs.jmedchem.1c00163

Scheme 4.

Scheme 4.

Synthesis of 9 and 10a

aReagents and conditions: (a) NaOH, MeOH, 25°C, 12h. (b) BH3-Me2S, THF, −78-25°C, 12.5h. (c) Dess-Martin, DCM, 25°C, 2h. (d) i. t-BuOK, 9: −20°C, 2h. 10: toluene, 70°C, 17h. ii. Pd/C, H2, MeOH, 25°C, 9: 2h, 10: 4h. (e) LiOH•H2O, MeOH, THF, H2O, 9: 25-70°C, 2h, 10: 70°C, 3h. (f) HATU, Et3N, THF, 25°C, 9: 12h, 10: 16h.