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. Author manuscript; available in PMC: 2017 Jul 14.
Published in final edited form as: J Med Chem. 2016 Jul 1;59(13):6531–6546. doi: 10.1021/acs.jmedchem.6b00760

Scheme 1.

Scheme 1

a) N-Boc-4-piperidinemethanol mesylate, Cs2CO3, DMF, 80 °C; b) N-Boc-3-azetidinemethanol mesylate, Cs2CO3, DMF, 80 °C; c) Na2CO3, Pd(PPh3)4, 6-ethoxy-2-naphthaleneboronic acid, H2O/DME, 80 °C (microwave); d) TFA/CH2Cl2 (1:1); e) sodium methoxide in MeOH, then 2% AcOH, formaldehyde or acetone, NaBH3CN; f) Ac2O, TEA, DMF.