Synthetic applications of 2-aryl-4-piperidones. XI1 a new synthesis of the E-azaeburnamine skeleton

Tetrahedron

Volumn 52, Issue 25, 1996, Pages 8581-8600

  López, Isabel ^a   Diez, Anna ^a   Rubiralta, Mario ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; INFRARED SPECTROSCOPY; METHYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0030013956     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00399-7     Document Type: Article

References (32)

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2. a) Rubiralta, M.; Diez, A.; Bosch, J.; Solans, X. J. Org. Chem., 1989, 54, 5591-5597;
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5. b) For a study on the synthesis and synthetic applications of 2-aryl-4-piperidones, see: "Piperidine. Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives", Rubiralta, M.; Giralt, E.; Diez, A., Elsevier Ed., Amsterdam, 1991, pp 313-421.
6. For the biogenetic numbering, see: a) Southon, I.W.; Buckingham, J. "Dictionary of Alkaloids", Chapman and Hall. London, 1989. p. xxxix;
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22. 16d However, these enones usually cyclize spontaneously to regenerate the piperidones. In the present case, a small amount of a pure compound was systematically isolated from the mixture obtained. From the complex spectral data that this anomalous compound showed, we could only infer that it was a dimeric structure, which we could not elucidate, not even with the MS spectrum and the 2D NMR experiments.
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24. 2:
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