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. Author manuscript; available in PMC: 2007 Dec 24.
Published in final edited form as: J Am Chem Soc. 2007 Mar 20;129(14):4175–4177. doi: 10.1021/ja068455x

Scheme 3. Synthesis of Plusbacin A3—The Final Stagesa.

Scheme 3

a (a) EDCI, HOBt, DIEA, THF, 91%; (b) 4 N HCl/dioxane, quantitative; then EDCI, HOBt, 5, DIEA, THF, 83%; (c) 4 N HCl, dioxane, quantitative; (d) EDCI, HOBt, 2, DIEA, DMF, 72%; (e) PdCl2(PPh3)2, Ph3SiH, CH2Cl2, 95%; (f) 4 N HCl, dioxane, quantitative; (g) EDCI, HOBt, 0 °C, DMF, 48 h, 72%; (h) 5% piperidine/DMF, quantitative; (i) N,N′-diBoc-N″-triflylguanidine, DIEA, DMF, 70%; (j) HF, anisole, 20% after HPLC purification.