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(A) Design of a potent cyclized, bivalent Smac peptidomimetic, compound 3. (B) Synthesis of compounds 3 and 4. Reagents and conditions: (a) (1) DIPEA/CH2Cl2/MeOH, (2) piperidine/20% DMF; (b) five cycles of Fmoc SPPS with HBTU/HOBt/DIPEA coupling; (c) (1) 1% TFA in DCM for 2 min 20 times, (2) HATU/HOAt/DIPEA in DCM; (d) 50% TFA in DCM for 2 h; (e) (1) Boc-N-methylalanine with EDC/HOAt/DCM for 12 h, (2) 50% TFA in DCM for 2 h.
