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. Author manuscript; available in PMC: 2020 Aug 1.
Published in final edited form as: Bioorg Med Chem. 2019 Jun 4;27(15):3254–3278. doi: 10.1016/j.bmc.2019.06.003

Scheme 14.

Scheme 14.

Methods used for the preparation of 23. Reagents and conditions: a) methyltriphenylphosphonium bromide, KOtBu, THF (81%); b) (i) BH3 TFA/DCM (79%); f) 20% Pd(OH)2/C, H2, ethanol (81%)THF, (ii) NaOH, H2O2 (77%); c) phthalimide PPh3, DIAD (91%); d) hydrazine monohydrate, methanol, reflux (74%); e) LiOH, THF; f) HOBT, EDC, DIPEA; g) 20% Pd(OH)2/C, H2, ethanol (97%); h) (i) BH3·THF, THF, (ii) Boc2O, DCM (49%); i) TFA, DCM (91%)