Electrophilic activation of lactams with Tf2O and pyridine: expedient synthesis of (+/-)-tetraponerine T4.
[reaction: see text] 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).
Charette
André B
AB
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada, H3C 3J7. andre.charette@umontreal.ca
Mathieu
Simon
S
Martel
Jonathan
J
D002384:Catalysis; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D011726:Pyridinium Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D000093843:Quinolizidine Alkaloids
D006575:Heterocyclic Compounds, 3-Ring; D007769:Lactams; D011725:Pyridines; D011726:Pyridinium Compounds; C512246:tetraponerine T4; D000093843:Quinolizidine Alkaloids