A stereoselective entry to tetrasubstituted quinolizidines and the puzzling structural assignment of the lupin alkaloid plumerinine

Synlett

Volumn , Issue 8, 2004, Pages 1343-1346

  Maldaner, Adriano O ^a   Pilli, Ronaldo A ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Cyclic N acyliminium ion; Intramolecular Michael reaction; Lupin alkaloid; Plumerinine; Tetrasubstituted quinolizidines; amidoalkylation

Indexed keywords

ALKALOID DERIVATIVE; PIPERIDINE; QUINOLIZIDINE DERIVATIVE;

ALKYLATION; ARTICLE; LUPIN; MICHAEL ADDITION; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; THERMODYNAMICS;

EID: 3142774923     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-825614     Document Type: Article

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23. -1 more stable than trans-fused quinolizidinone 16).
24. 3, MeOH, 60°C) were previously used to carry out epimerization in quinolizidinone and indolizidinone systems (see ref. 8).
25. 2O): δ = 3.99 (m, 1 H), 3.78 (m, 1 H), 3.65 (dt, J = 13.2, 3.6 Hz, 1 H), 3.32 (ddd, J = 10.1, 5.1, 2.5 Hz, 1 H), 2.11 (m, 1 H), 1.85-2.05 (m, 3 H), 1.81 (m, 1 H), 1.58-1.73 (m, 3 H), 1.35-1.48 (m, 2 H), 1.17 (d, J = 6.4 Hz, 3 H), 0.89 (d, J = 6.4 Hz, 3 H), 0.88 (d, J = 6.4 Hz, 3 H), 0.78 (d, J = 6.8 Hz, 3 H).