Rhodium-catalyzed intramolecular conjugate addition of vinylstannanes to dihydro-4-pyridones: a simple method for stereoselective construction of 1-azabicyclic alkaloids

Tetrahedron

Volumn 64, Issue 16, 2008, Pages 3464-3470

  Furman, Bartłomiej ^a   Lipner, Grzegorz ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Dihydropyridones; Quinolizidines; Rhodium complexes; Vinylstannanes

Indexed keywords

ALKALOID DERIVATIVE; ALKENE; PYRIDONE DERIVATIVE; RHODIUM DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; COMPLEX FORMATION; CONJUGATION; METHODOLOGY; PRIORITY JOURNAL; ROOM TEMPERATURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 39849085058     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.021     Document Type: Article

References (31)

1. Corey E.J., and Wollenberg R.H. J. Am. Chem. Soc. 96 (1974) 5581-5583
2. Dodd D.S., Pierce H.D., and Oehlschlager A.C. J. Org. Chem. 57 (1992) 5250-5253
3. Corriu R.J.P., Geng B., and Moreau J.J. J. Org. Chem. 58 (1993) 1443-1448
4. Piers E., McEachern E.J., and Burns P.A. J. Org. Chem. 60 (1995) 2322-2323
5. Piers E., Gladstone P.L., Yee J.G.K., and McEachern E.J. Tetrahedron 54 (1998) 10609-10626
6. Piers E., McEachern E.J., and Burns P.A. Tetrahedron 56 (2000) 2753-2765
7. Farina V., Krishnamurthy V., and Scott W.J. The Stille Reaction (1998), Wiley, New York, NY
8. Domínguez B., Pazos Y., and De Lera A.R. J. Org. Chem. 65 (2000) 5917-5925
9. Suffert J., Salem B., and Klotz P. J. Am. Chem. Soc. 123 (2001) 12107-12108
10. Brown M.A., and Kerr M.A. Tetrahedron Lett. 42 (2001) 983-985
11. Li C., Pace E.A., Liang M.-C., Lobkovsky E., Gilmore T.D., and Porco J.A. J. Am. Chem. Soc. 123 (2001) 11308-11309
12. Clarke P.A., Davie R.L., and Peace S. Tetrahedron Lett. 43 (2002) 2753-2756
13. Oi S., Moro M., Ono S., and Inoue Y. Chem. Lett. (1998) 83-85
14. Huang T.S., and Li C.J. Org. Lett. 3 (2001) 2037-2039
15. Venkatraman S., Meng Y., and Li C.J. Tetrahedron Lett. 42 (2001) 4459-4462
16. Huang T.S., Meng Y., Venkatraman S., Wang D., and Li C.J. J. Am. Chem. Soc. 123 (2001) 7451-7452
17. El Nemr A. Tetrahedron 56 (2000) 8579-8629
18. Michael J.P. Nat. Prod. Rep. 24 (2007) 191-222 and previous reports from this author
19. Laschat S., and Dickner T. Synthesis (2000) 1781-1813
20. Buffat M.G.P. Tetrahedron 60 (2004) 1701-1729
21. Dziedzic M., Małecka M., and Furman B. Org. Lett. 7 (2005) 1725-1727
22. Maison W., and Prenzel A.H.G.P. Synthesis (2005) 1031-1045
23. Crystallographic data for the structure 18a in this paper has been deposited with the Cambridge Crystallographic Data Centre as a supplementary publication number CCDC 664018. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 1223 336033 or e-mail: deposit@ccdc.com.ac.uk].
24. He H., Shen B., and Carter G.T. Tetrahedron Lett. 41 (2000) 2067-2071
25. Tehrani K.A., D'hooghe M., and De Kimpe N. Tetrahedron 59 (2003) 3099-3108
26. Barluenga J., Mateos C., Anzar F., and Valdés C. J. Org. Chem. 69 (2004) 7114-7122
27. For selected examples of racemic synthesis of lasubines, see:
28. Ent H., De Koning H., and Speckamp W.N. Heterocycles 27 (1988) 237-243
29. Bardot V., Gardette D., Gelas-Mialhe Y., Gramain J.-C., and Remuson R. Heterocycles 48 (1998) 507-518
30. Zaja M., and Blechert S. Tetrahedron 60 (2004) 9629-9634
31. Piers E., Walker S.D., and Ambrust R. J. Chem. Soc., Perkin Trans. 1 (2000) 635-637