A new class of tröger's base analogues bearing spiro[4.5] lactone straps

Synthesis

Volumn , Issue 4, 2009, Pages 636-642

  Mahon, Andrew B ^a   Craig, Donald C ^b   Try, Andrew C ^a  

^a MACQUARIE UNIVERSITY   (Australia)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

Amines; Cyclization; Lactones; Spiro compounds; Tr ger's base

Indexed keywords

CARBOXYLIC ACID DERIVATIVES; DICARBOXYLIC ACIDS; DICYCLOHEXYLCARBODIIMIDE; LACTONES; NEW CLASS; SPIRO COMPOUNDS;

AMINATION; CARBOXYLIC ACIDS; CYCLIZATION; ORGANIC ACIDS;

AMINES;

AZOCINE DERIVATIVE; BASE; CARBOXYLIC ACID DERIVATIVE; CHLORIDE; DICYCLOHEXYLCARBODIIMIDE; LACTONE DERIVATIVE; PHTHALOYL DICHLORIDE; TROGER BASE; UNCLASSIFIED DRUG;

ARTICLE;

EID: 63849092343     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1083341     Document Type: Article

References (36)

1. Adrian, J. C. Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1989, 111, 8055.
2. Webb, T. H.; Wilcox, C. S. J. Org. Chem. 1990, 55, 363.
3. Crossley, M. J.; Mackay, L. G.; Try, A. C. J. Chem. Soc., Chem. Commun. 1995, 1925.
4. Hansson, A. P.; Norrby, P.-O.; Wärnmark, K. Tetrahedron Lett. 1998, 39, 4565.
5. Goswami, S.; Ghosh, K.; Dasgupta, S. J. Org. Chem. 2000, 65, 1907.
6. Goldberg, Y.; Alper, H. Tetrahedron Lett. 1995, 36, 369.
7. Harmata, M.; Kahraman, M. Tetrahedron: Asymmetry 2000, 11, 2875.
8. Jensen, J.; Wärnmark, K. Synthesis 2001, 1873.
9. Jensen, J.; Tejler, J.; Warnmark, K. J. Org. Chem. 2002, 67, 6008.
10. Li, Z. H.; Xu, X.; Peng, Y.; Jiang, Z.; Ding, C.; Qian, X. Synthesis 2005, 1228.
11. Hof, F.; Schar, M.; Scofield, D. M.; Fischer, F.; Diederich, F.; Sergeyev, S. Helv. Chim. Acta 2005, 88, 2333.
12. Solano, C.; Svensson, D.; Olomi, Z.; Jensen, J.; Wendt, O. F.; Warnmark, K. Eur. J. Org. Chem. 2005, 3510.
13. Crossley, M. J.; Hambley, T. W.; Mackay, L. G.; Try, A. C.; Walton, R. J. Chem. Soc., Chem. Commun. 1995, 1077.
14. Moreno-Fuquen, R.; Abonia, R.; Valderrama-Naranjo, J.; Albornoz, A.; Mariezcurrena, R. A. Acta Crystallogr., Sect. C 2001, 57, 281.
15. Abonia, R.; Albornoz, A.; Larrahondo, H.; Quiroga, J.; Insuasty, B.; Insuasty, H.; Hormaza, A.; Sanchez, A.; Nogueras, M. J. Chem. Soc., Perkin Trans. 1 2002, 1588.
16. Kobayashi, T.; Moriwaki, T.; Tsubakiyama, M.; Yoshida, S. J. Chem. Soc., Perkin Trans. 1 2002, 1963.
17. Valík, M.; Dolensk, B.; Pertrickova, H.; Vasek, P.; Král, V. Tetrahedron Lett. 2003, 44, 2083.
18. Weber, E.; Müller, U.; Worsch, D.; Vögtle, F.; Will, G.; Kirfel, A. J. Chem. Soc., Chem. Commun. 1985, 1578.
19. Bond, D. R.; Scott, J. L. J. Chem. Soc., Perkin Trans. 2 1991, 47.
20. Tatibouët, A.; Demeunynck, M.; Salez, H.; Arnaud, R.; Lhomme, J.; Courseille, C. Bull. Soc. Chim. Fr. 1997, 134, 495.
21. Harmata, M.; Carter, K. W.; Jones, D. E.; Kahraman, M. Tetrahedron Lett. 1996, 37, 6267.
22. Harmata, M.; Rayanil, K.-O.; Barnes, C. L. Supramol. Chem. 2006, 18, 581.
23. Cooper, F. C.; Partridge, M. W. J. Chem. Soc. 1957, 2888.
24. Greenberg, A.; Molinaro, N.; Lang, M. J. Org. Chem. 1984, 49, 1127.
25. Johnson, R. A.; Gorman, R. R.; Wnuk, R. J.; Crittenden, N. J.; Aiken, J. W. J. Med. Chem. 1993, 36, 3202.
26. Lenev, D. A.; Chervin, I. I.; Lyssenko, K. A.; Kostyanovsky, R. G. Tetrahedron Lett. 2007, 48, 3363.
27. Mahon, A. B.; Craig, D. C.; Try, A. C. ARKIVOC 2008, (xii), 148.
28. Hamada, Y.; Mukai, S. Tetrahedron: Asymmetry 1996, 7, 2671.
29. Faroughi, M.; Try, A. C.; Klepetko, J.; Turner, P. Tetrahedron Lett. 2007, 48, 6548.
30. Faroughi, M.; Try, A. C.; Turner, P. Acta Crystallogr., Sect. E 2008, 64, o39.
31. Faroughi, M.; Try, A. C.; Turner, P. Acta Crystallogr., Sect. E 2008, 64, o458.
32. Spielman, M. A. J. Am. Chem. Soc. 1935, 57, 583.
33. Miller, T. R.; Wagner, E. C. J. Am. Chem. Soc. 1941, 63, 832.
34. Cooper, F. C.; Partridge, M. W. J. Chem. Soc. 1955, 991.
35. Faroughi, M.; Try, A. C.; Turner, P. Acta Crystallogr., Sect. E 2006, 62, o3893.
36. O'Mahony, M. J.; Rees, C. W.; Saville-Stones, E. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 1459.