Synthesis of novel unsaturated bicyclic lactams by ring-closing metathesis

Synlett

Volumn , Issue 10, 1999, Pages 1660-1662

  Grossmith, Catharine E ^b   Senia, Francesco ^c   Wagner, Jürgen ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

^b UNIVERSITY OF BATH   (United Kingdom)

^c NONE

Author keywords

Bicyclic compounds; Lactams; Metathesis; Ruthenium

Indexed keywords

ALKENE DERIVATIVE; BICYCLO COMPOUND; LACTAM;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032826155     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2887     Document Type: Article

References (19)

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2. For a recent comprehensive review, see: Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W.D. Tetrahedron 1997, 53, 12789 and references cited therein.
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6. McClure, K.F.; Renold, P.; Kemp, D.S. J. Org. Chem. 1995, 60, 454.
7. +.
8. +.
9. Schwab, P.; France, M.B.; Ziller, J.W.; Grubbs, R.H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039. For recent reviews on the ring-closing metathesis reaction, see: Amstrong, S.K. J. Chem. Soc., Perkin Trans. I 1998, 371. Grubbs, R.H.; Chang, S. Tetrahedron 1998, 54, 4413. Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. Grubbs, R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995, 28, 446.
10. Schwab, P.; France, M.B.; Ziller, J.W.; Grubbs, R.H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039. For recent reviews on the ring-closing metathesis reaction, see: Amstrong, S.K. J. Chem. Soc., Perkin Trans. I 1998, 371. Grubbs, R.H.; Chang, S. Tetrahedron 1998, 54, 4413. Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. Grubbs, R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995, 28, 446.
11. Schwab, P.; France, M.B.; Ziller, J.W.; Grubbs, R.H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039. For recent reviews on the ring-closing metathesis reaction, see: Amstrong, S.K. J. Chem. Soc., Perkin Trans. I 1998, 371. Grubbs, R.H.; Chang, S. Tetrahedron 1998, 54, 4413. Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. Grubbs, R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995, 28, 446.
12. Schwab, P.; France, M.B.; Ziller, J.W.; Grubbs, R.H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039. For recent reviews on the ring-closing metathesis reaction, see: Amstrong, S.K. J. Chem. Soc., Perkin Trans. I 1998, 371. Grubbs, R.H.; Chang, S. Tetrahedron 1998, 54, 4413. Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. Grubbs, R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995, 28, 446.
13. Schwab, P.; France, M.B.; Ziller, J.W.; Grubbs, R.H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039. For recent reviews on the ring-closing metathesis reaction, see: Amstrong, S.K. J. Chem. Soc., Perkin Trans. I 1998, 371. Grubbs, R.H.; Chang, S. Tetrahedron 1998, 54, 4413. Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037. Grubbs, R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995, 28, 446.
14. 6) did not improve the conversion. Similar difficulties have been encountered by others, see: Kirkland, T.A.; Grubbs, R.H. J. Org. Chem. 1997, 62, 7310.
15. For a related application of the ring-closing metathesis reaction, see: Beal, L.M.; Moeller, K.D. Tetrahedron Lett. 1998, 39, 4639. For other types of bicyclic lactams, see: Martin, S.F.; Chen, H.-J.; Courtney, A.K.; Liao, Y.; Plätzel, M.; Ramser, M.N.; Wagman, A.S. Tetrahedron 1996, 52, 7251. Diedrichs, N.; Westermann, B. Synlett 1999, 7, 1127. Tarling, C.A.; Holmes, A.B.; Markwell, R.E.; Pearson, N.D. J. Chem. Soc., Perkin Trans. I 1999, 1695.
16. For a related application of the ring-closing metathesis reaction, see: Beal, L.M.; Moeller, K.D. Tetrahedron Lett. 1998, 39, 4639. For other types of bicyclic lactams, see: Martin, S.F.; Chen, H.-J.; Courtney, A.K.; Liao, Y.; Plätzel, M.; Ramser, M.N.; Wagman, A.S. Tetrahedron 1996, 52, 7251. Diedrichs, N.; Westermann, B. Synlett 1999, 7, 1127. Tarling, C.A.; Holmes, A.B.; Markwell, R.E.; Pearson, N.D. J. Chem. Soc., Perkin Trans. I 1999, 1695.
17. For a related application of the ring-closing metathesis reaction, see: Beal, L.M.; Moeller, K.D. Tetrahedron Lett. 1998, 39, 4639. For other types of bicyclic lactams, see: Martin, S.F.; Chen, H.-J.; Courtney, A.K.; Liao, Y.; Plätzel, M.; Ramser, M.N.; Wagman, A.S. Tetrahedron 1996, 52, 7251. Diedrichs, N.; Westermann, B. Synlett 1999, 7, 1127. Tarling, C.A.; Holmes, A.B.; Markwell, R.E.; Pearson, N.D. J. Chem. Soc., Perkin Trans. I 1999, 1695.
18. For a related application of the ring-closing metathesis reaction, see: Beal, L.M.; Moeller, K.D. Tetrahedron Lett. 1998, 39, 4639. For other types of bicyclic lactams, see: Martin, S.F.; Chen, H.-J.; Courtney, A.K.; Liao, Y.; Plätzel, M.; Ramser, M.N.; Wagman, A.S. Tetrahedron 1996, 52, 7251. Diedrichs, N.; Westermann, B. Synlett 1999, 7, 1127. Tarling, C.A.; Holmes, A.B.; Markwell, R.E.; Pearson, N.D. J. Chem. Soc., Perkin Trans. I 1999, 1695.
19. Compound 7 has been prepared previously in 11 steps from L-pyroglutamic acid: Hanessian, S.; Ronan, B.; Laoui, A. Bioorg. Med. Chem. Lett. 1994, 4, 1397.