Synthesis of pyridine fused polycyclic amines using sequential ring-closing metathesis and radical cyclisation reactions

Tetrahedron Letters

Volumn 44, Issue 14, 2003, Pages 2995-2999

  Baker, S Richard ^a   Cases, Manuel ^a   Keenan, Martine ^a   Lewis, Richard A ^a   Tan, Paul ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; NITROGEN; PYRIDINE;

ARTICLE; CATALYST; CYCLIZATION; MOLECULAR INTERACTION; RING CLOSING METATHESIS; SYNTHESIS;

EID: 0037474654     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00389-7     Document Type: Article

References (16)

1. Paquette L.A., Leit S.M. J. Am. Chem. Soc. 121:1999;8126-8127.
2. For a leading review of radical cyclisations, see: Giese B., Kopping B., Gobel T., Dickhaut J., Thoma G., Kulicke K.J., Trach F. Organic Reactions. 48:1996;301-856 John Wiley, New York.
3. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056; (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043; (e) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529.
4. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056; (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043; (e) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529.
5. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056; (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043; (e) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529.
6. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056; (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043; (e) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529.
7. For reviews of RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450; (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056; (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043; (e) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529.
8. Evans D.A., Campos K.R., Tedrow J.S., Michael F.E., Gagné M.R. J. Org. Chem. 64:1999;2994-2995.
9. For synthesis, see: (a) Estel, L.; Marsais, F.; Queguiner, G. J. Org. Chem. 1988, 53, 2740-2744; (b) Marsais, F.; Pineau, Ph.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Queguiner, G. J. Org. Chem. 1992, 57, 565-573.
10. For synthesis, see: (a) Estel, L.; Marsais, F.; Queguiner, G. J. Org. Chem. 1988, 53, 2740-2744; (b) Marsais, F.; Pineau, Ph.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Queguiner, G. J. Org. Chem. 1992, 57, 565-573.
11. Tamaru Y., Yamada Y., Yoshida Z. J. Org. Chem. 43:1978;3396-3398.
12. Evans P., Grigg R., Ramzan M.I., Sridharan V., York M. Tetrahedron Lett. 40:1999;3021-3024.
13. Grigg R., Sridharan V., York M. Tetrahedron Lett. 39:1998;4139-4142.
14. Mancuso A.J., Swern D. Synthesis. 1981;165-185.
15. Bowers Nemia M.M., Lee J., Joullie M.M. Synth. Commun. 13:1983;1117-1123.
16. +].