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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 1.

Scheme 1

Synthesis of the Spermidine/Spermine series of N-alkylpolyamines

Reagents:

a. (i)CH2=CHCN, MeOH, r.t, 15h; (ii) Boc2O (excess), MeOH, r.t, 12h.

b. AcOH, Pd(OH)2/C, H2, 50 psi; Boc2O (excess), MeOH, r.t, 12h.

c. (i) 1,4-Diaminobutane (excess), Pd(OH)2/C, H2, 60 psi; (ii) Boc2O (excess), MeOH, r.t, 12 h.

d. CF3CO2H (excess), r.t.

e. (i) CF3COOEt (1or 2 Eq.), MeOH. −78°C to 0° C, 1h; (ii) Boc2O (excess); (iii) LiOH, THF, r.t.

f. (i) CH2=CHCN (2 Eq.), MeOH, r.t, 15 h; (ii) Boc2O (excess), MeOH, r.t, 12h.

g. AcOH, Pd(OH)2/C, H2, 50 psi; Boc2O (excess), MeOH, r.t, 12 h.

h. NaH, C16H33I, DMF, −15°C-r.t, 24h.