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. Author manuscript; available in PMC: 2020 Oct 16.
Published in final edited form as: Bioorg Med Chem. 2010 May 25;18(14):5208–5223. doi: 10.1016/j.bmc.2010.05.057

Scheme 1.

Scheme 1.

Solid phase synthesis of spirodiketopiperazines 1a, 1b, 2–18, 23, 25, 26, and 28. Reagents and conditions: (a) THF/MeOH (1:1), 65 ”C; (b) Pd(PPh3)4, Bu3SnH, AcOH/CH2Cl2, rt; (c) Ar-CHO, NaBH(OAc)3, AcOH/DMF; (d) TFA/CH2Cl2 (1:1); (e) AcOH/toluene, 90 °C and then 4 N HCl/AcOEt; (f) 2 N NaOH, MeOH; (g) MsCl, Et3N, CH2Cl2; (h) potassium phthalimide, DMF, 70 °C; (i) NH2NH2·H2O, EtOH, then concd HCl, reflux.