Enantioselective access to Lobelia alkaloids

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4528-4532

  Compère, Delphine ^a   Marazano, Christian ^a   Das, Bhupesh C ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 [6 (2 HYDROXY 2 PHENYLETHYL) 1 METHYL 1,2,5,6 TETRAHYDROPYRIDIN 2 YL] 1 PHENYLETHANONE; 2 [6 (2 HYDROXY 2 PHENYLETHYL) 1 METHYLPIPERIDIN 2 YL] 1 PHENYLETHANONE; ALKALOID DERIVATIVE; LOBELINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DIASTEREOISOMER; DRUG HYDROLYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0242705214     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981912a     Document Type: Article

References (22)

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2. For a recent X-ray study of (-)-lobeline hydrobromide and hydrochloride, see: Glaser, R.; Hug, P.; Drouin, M.; Michael, A. J. Chem. Soc., Perkin Trans. 2 1992, 1071.
3. The synthesis of (-)-lobeline itself has not yet been reported, but in a series of papers, Hootelé et al. have reported the syntheses of related sedum alkaloids. These compounds were obtained as racemates or as pure enantiomers using advanced chiral precursors of natural origin or obtained by resolution. See inter alia: (a) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 1. (b) Ibebeke-Bomangwa, W.; Hootelé, C. Tetrahedron 1987, 43, 935. (c) Halin, F.; Slosse, P.; Hootelé, C. Tetrahedron 1985, 41, 2891.
4. The synthesis of (-)-lobeline itself has not yet been reported, but in a series of papers, Hootelé et al. have reported the syntheses of related sedum alkaloids. These compounds were obtained as racemates or as pure enantiomers using advanced chiral precursors of natural origin or obtained by resolution. See inter alia: (a) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 1. (b) Ibebeke-Bomangwa, W.; Hootelé, C. Tetrahedron 1987, 43, 935. (c) Halin, F.; Slosse, P.; Hootelé, C. Tetrahedron 1985, 41, 2891.
5. The synthesis of (-)-lobeline itself has not yet been reported, but in a series of papers, Hootelé et al. have reported the syntheses of related sedum alkaloids. These compounds were obtained as racemates or as pure enantiomers using advanced chiral precursors of natural origin or obtained by resolution. See inter alia: (a) Driessens, F.; Hootelé, C. Can. J. Chem. 1991, 69, 1. (b) Ibebeke-Bomangwa, W.; Hootelé, C. Tetrahedron 1987, 43, 935. (c) Halin, F.; Slosse, P.; Hootelé, C. Tetrahedron 1985, 41, 2891.
6. Wong, Y.-S.; Marazano, C.; Dino Gnecco, D.; Génisson, Y.; Chiaroni, A.; Das, B. C. J. Org. Chem. 1997, 62, 729 and references therein.
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12. The yield is lower in these series as a result of a competing ring opening of the nitrogen heterocycle when isomer 14 was treated with t-BuOK.
13. For an enantioselective synthesis and main references, see: Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035.
14. For an enantioselective synthesis and leading references, see: Oppolzer, W.; Deerberg, J.; Tamura, O. Helv. Chim. Acta 1994, 77, 554.
15. (a) Grierson, D. S.; Harris, M.; Husson, H.-P. J. Am. Chem. Soc. 1980, 102, 1064-1082.
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19. The crude product of the phenyllithium addition consists of a mixture of 2a and 2b in a 3:2 to 2:1 ratio, which reflected approximately the diastereoisomeric ratio observed for adduct 17. We attributed the 2,6-trans stereochemistry to isomer 2a by comparison with the reported structure of a closely related natural product, (-)-sedacrine: Colau, B.; Hootelé, C. Can. J. Chem. 1983, 61, 470.
20. For epimerization of related β-amino-ketone derivatives, see: Durant, A.; Hootelé, C. Can. J. Chem. 1992, 70, 2722. Colau, B.; Hootelé, C. Can. J. Chem. 1983, 61, 470. Barringer, D. F.; Berkelhammer, G.; Carter, S. D.; Goldman, L.; Lanzilotti, A. E. J. Org. Chem. 1973, 38, 1933.
21. For epimerization of related β-amino-ketone derivatives, see: Durant, A.; Hootelé, C. Can. J. Chem. 1992, 70, 2722. Colau, B.; Hootelé, C. Can. J. Chem. 1983, 61, 470. Barringer, D. F.; Berkelhammer, G.; Carter, S. D.; Goldman, L.; Lanzilotti, A. E. J. Org. Chem. 1973, 38, 1933.
22. For epimerization of related β-amino-ketone derivatives, see: Durant, A.; Hootelé, C. Can. J. Chem. 1992, 70, 2722. Colau, B.; Hootelé, C. Can. J. Chem. 1983, 61, 470. Barringer, D. F.; Berkelhammer, G.; Carter, S. D.; Goldman, L.; Lanzilotti, A. E. J. Org. Chem. 1973, 38, 1933.