Journal of Organic Chemistry p. 2092 - 2100 (1994)
Update date:2022-07-30
Topics:
Marquart, Angela L.
Podlogar, Brent L.
Huber, Edward W.
Demeter, David A.
Peet, Norton P.
et al.
Treatment of the amido esters 9 and 17 with PPSE (polyphosphoric acid trimethylsilyl ester) followed by NaBH4 in ethanol gave the quinolizidinones 11-14 and 19 via a vinylogous Bischler-Napieralski nitrilium ion cyclization-reductive lactamization two-step process.Subsequent ozonolysis and reduction afforded chiral hydroxylated quinolizidines in moderate to good yield.In contrast to five-membered-ring formation, six-membered-ring formation via nitrilium-ion cyclization requires a p-methoxy-substituted styryl terminator.The effect para-substituted styryl terminators have on the energy of activation and ΔH for the cyclization process has been calculated by semiempirical and ab initio methods.
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