ol052069n_si_002.cif (38.88 kB)

Electrophilic Activation of Lactams with Tf2O and Pyridine:  Expedient Synthesis of (±)-Tetraponerine T4

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posted on 24.11.2005 by André B. Charette, Simon Mathieu, Jonathan Martel
The electrophilic activation of lactams with triflic anhydride in the presence of pyridine was investigated by NMR. It was found that 2-pyrrolidone led to the clean formation of the corresponding pyridinium imidate in 89% isolated yield. The subsequent nucleophilic addition of organometallic reagents led to 2-substituted dihydropyridines. A synthesis of (±)-tetraponerine T4 with three simple building blocks was accomplished in 3 steps (38% yield).