Molecular topology: The synthesis of a new class of rigid arc-shaped spacer molecules based on syn-facially fused norbornanes and 7- heteronorbornanes in which heterobridges are used to govern backbone curvature

Tetrahedron Letters

Volumn 40, Issue 21, 1999, Pages 4111-4114

  Warrener, Ronald N ^a   Margetic, Davor ^a   Sun, Guanxing ^a   Amarasekara, Ananda S ^a   Foley, Patrick ^a   Butler, Douglas N ^a   Russell, Richard A ^b  

^a CENTRAL QUEENSLAND UNIVERSITY   (Australia)

^b DEAKIN UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE;

ARTICLE; AUSTRALIA; DRUG STRUCTURE; DRUG SYNTHESIS; GEOMETRY;

EID: 0033591182     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00694-2     Document Type: Article

References (12)

1. 1. J.-M. Jehn, "Supramolecular Chemistry", VCH, Weinheim, 1995.
2. 2. Margetic, D.; Johnston, M. R.; Tiekink, E. R. T.; Warrener, R. N. Tetrahedron Lett., 1998, 39, 5277-5281.
3. 3. Paddon-Row, M. N.; Cotsaris, E.; Patney, H. K. Tetrahedron 1986, 42, 1779-1788.
4. 8 have reported the synthesis of [6]poly(bicyclo[2.2.2]octanes) which also have a curved topology.
5. 5. Sasaki, T.; Manabe, T.; Nishida, S. J. Org. Chem. 1980, 476-479.
6. 6. Warrener, R. N.; Butler, D. N.; Liao, W. Y.; Pitt, I. G.; Russell, R. A. Tetrahedron Lett., 1991, 32, 1889-1892.
7. 7. Vasiliev, N. V.; Lyashenko, Y. E.; Kolomietz, A. F.; Sokolskii, G. A. Khim. Geterotsikl Soedin., 1987, 562;
8. 8. Grimme, W.; Gossell, J.; Lek, J. Angew. Chem. Int. Ed., 1998, 37, 473-475.
9. 9 ACE coupling: Warrener, R.N.; Schultz, A.C.; Butler, D.N.; Wang S.; Mahadevan, I.B.; Russell, R.A. Chem. Commun., 1997, 1023-1024.
10. 10. Aza-ACE coupling: Butler, D. N.; Malpass, J. R.; Margetic, D.; Russell, R. A.; Sun, G.; Warrener, R. N. Synlett, 1998, 588-589.
11. 3), 13 1.94, s, 2H; 2.27, s, 4H; 3.29, s, 2H; 3.83, s, 6H. 14 2.60, s, 4H; 3.83, s, 12H; 5.68, s, 2H. 15 1.90, s, 2H; 2.15, s, 4H; 3.30, s, 2H; 3.72, s, 12H; 3.99, s, 4H, 7.22-7.44, m, 10H. 16 2.46, s, 4H; 3.74, s, 12H; 4.02, s, 4H; 5.78, s 2H; 7.31, m, 10H. 17 0.99, d J=8.7 Hz, 2H; 1.93, s, 2H; 1.95, s, 4H; 2.03, s, 12H; 2.32, d J=8.7 Hz, 2H; 2.62, s, 4H; 3.83, s, 12H; 6.11s, 4H. 18 1.39, d J=9.0 Hz, 2H; 1.61, m, 2H; 1.77, s, 4H; 1.86, s, 4H; 2.07, d, J=11 Hz, 2H; 2.30, s, 4H; 2.41, s, 4H, 2.70, d, J=9.0 Hz, 2H; 3.59, s, 4H, 3.96, s, 24H, 7.44-7.46, m, 4H,; 8.05-8.06, m, 4H. 19 0.70, d J=8.1 Hz, 2H; 1.80, s, 2H; 1.83, s, 4H; 1.91, s, 4H; 2.18, s, 2H; 2.55, d J=8.1 Hz, 2H; 2.56, s, 4H; 3.79, s, 12H; 4.15, s, 4H; 6.07, s, 4H; 7.14-7-42, m, 10H; 20 2.00, s, 4H; 2.09, s, 4H; 3.68, s, 12H; 4.08, br s, 4H; 4.55, s, 2H; 5.29, s, 4H; 7.11-7.30, m, 14H; 7.70, d J=7.3Hz, 4H.
12. 12. Warrener, R. N.; Amarasekara, A. S.; Russell, R. A., 1998, unpublished result.