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. Author manuscript; available in PMC: 2013 Jul 3.
Published in final edited form as: Bioorg Med Chem Lett. 2009 Mar 18;19(9):2478–2481. doi: 10.1016/j.bmcl.2009.03.055

Scheme 2.

Scheme 2

Synthesis of the Norspermidine/Norspermine series.

Reagents: a. Boc2O (excess), MeOH, rt, 12 h. b. NaH (excess), C16H33I, DMF, − 15°C-r.t., 24 h. c. TFA, r.t, 45 min d. (i) CF3COOEt, MeOH, −78 °C to 0 °C, 1h; (ii) Boc2O (excess), MeOH, r.t, 12 h; (iii) LiOH,THF, r.t. e. 3-bromopropan-1-ol, K2CO3, DMF, 60°C (ii) Boc2O (excess), MeOH, r.t, 12h. f. (i) MeOH, Pd(OH)2/C, H2, 60 psi; (ii) Boc2O (excess), MeOH, r.t, 12h. g. PCC, DCM, r.t. h. (i)C16H33NH2, NaCNBH3, glacial AcOH (5 drops), anhyd. MeOH, r.t, 24h (ii) Boc2O (excess), MeOH, r.t, 12h. i. i) CH2CHCN, MeOH, r.t, 6 h; ii) Boc2O (excess), MeOH, rt, 12 h. j. i) Pd(OH)2/C, Glacial acetic acid, H2, 60 psi; ii) Boc2O (excess), MeOH, rt, 12 h.