Concise Enantiospecific Synthesis of a Coccinellied Alkaloid, (-)-adalinine

Organic Letters

Volumn 2, Issue 24, 2000, Pages 3925-3927

  Honda, Toshio ^a   Kimura, Mika ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADALININE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PIPERIDINE DERIVATIVE; SAMARIUM;

ANIMAL; ARTICLE; BEETLE; CHEMISTRY; HYDROLYSIS; STEREOISOMERISM; SYNTHESIS;

ANIMALS; BEETLES; HYDROLYSIS; INDICATORS AND REAGENTS; PIPERIDINES; SAMARIUM; STEREOISOMERISM;

EID: 0034736362     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006712b     Document Type: Article

References (10)

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2. Yamazaki, N.; Ito, T.; Kibayashi, C. Tetrahedron Lett. 1999, 40, 739.
3. (a) Broeders, F.; Braekman, J. C.; Daloze, D. Bull. Soc. Chim. Belg. 1997, 106, 377.
4. (b) Yamazaki, N.; Ito, T.; Kibayashi, C. Synlett 1999, 37.
5. Honda, T.; Ishikawa, F. Chem. Commun. 1999, 1065.
6. For a recent review of the coccinellied alkaloids, see: King, A. G.; Meinwald, J. Chem. Rev. 1996, 96, 1105.
7. Peterson, J. S.; Fels, G.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 4539.
8. Roth, M.; Dubs, P.; Götschi, E.; Eschenmoser, A. Helv. Chim. Acta 1971, 54, 710.
9. For Michael addition of Grignard reagent to enaminones, see: Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182.
10. A small amount of uncyclized δ-amino ester could also be isolated from this reaction; however, the uncyclized compound was easily transformed to the cyclization product by heating in benzene or by standing at room temperature for few days. The yield was demonstrated as the combined yield.