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. Author manuscript; available in PMC: 2014 Dec 1.
Published in final edited form as: Bioorg Med Chem Lett. 2013 Sep 21;23(23):10.1016/j.bmcl.2013.09.043. doi: 10.1016/j.bmcl.2013.09.043

Scheme 1.

Scheme 1

Synthesis of PS-341-BP-1

Key: (a) SeO2, H2O, pyridine, 68%; (b) MeOH, HCl gas, 94%; (c) MeOH, NaOH, 73%; (d) 5, TBTU, DIEA, DMF, 60%; (e) LiOH, THF/MeOH/H2O, 47%; (f) (i) NHS, DCC, DME; (ii) alendronate, DIEA, 2-propanol/H2O; (iii) (2-methylpropyl)boronic acid, MeOH/Hexane/2M HCl