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Synthesis of aspidosperma alkaloids by interception of diiminium ion 5: a) Tf2O, 3-cyanopyridine, MeCN, 85 °C. i) NaBH3CN, THF, 50%. ii) 4-(Me2N)-C6H4MgBr, −40 °C; Red-Al, 40%. iii) trifluoroacetic acid, sodium trifluoroacetate, H2O, 70 °C, 57%. b) H2, Pt/C, THF, 100%. c) H2, Pt/C, THF. d) LiAlH4, THF, 65 °C, 82% (two steps). Tf2O = trifluoromethanesulfonic anhydride.
