Fundamental principles of block design and assembly in the production of large, rigid molecules with functional units (effectors) precisely located on a carbocyclic framework

Synlett

Volumn , Issue 6, 1998, Pages 566-573

  Warrener, Ronald N ^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

EID: 0002514571     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-3133     Document Type: Article

References (59)

1. Building BLOCKS in Synthesis, Part 2; for part 1, see reference 6.
2. BLOCK was not considered as an acronym when used in this study, but if required, the following colloquial Australian one would seem suitable "Bonzer Little Organic Construction Kit" (Bonzer is a slang term for good, excellent).
3. The term 'effector' is used as a generic descriptor of any group or functional unit that has a special role in the use of the molecule and covers chromophores, biological activity, reporter groups, colour agents, light absorbers, quenchers, ligands, crown ethers, porphyrins, heterocyclics, solubility modifiers, pharmacophores, etc.
4. 8 (Matrix Presented)
5. Rigid and semirigid, fused molecular structures act as racks (hence the generic name 'molrac') upon which functionality can be placed in geometrically precise positions, see Warrener, R. N. Chem Aust. 1992, 578.
6. Warrener, R. N.; Schultz, A. C.; Butler, D. N.; Wang, S.; Mahadevan, I. B.; Russell, R. A. Chem. Commun. 1997, 1023.
7. Dewar, J. Proc. Royal Soc. Edinburgh 1867, 6, 82 and 86.
8. Stoddart, F. Chem. in Britain 1988, 1203.
9. Matthias, J. P.; Stoddart, F. Chem. Soc. Rev. 1992, 215.
10. Kasynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601.
11. Lindsey, J. S.; Prathapan, S.; Johnston, T. E.; Wagener, R. W. Tetrahedron 1994, 50, 8941.
12. Tomalia, D. A. Aldrichimica Acta. 1993, 26, 91.
13. Wenz, G. Angew Chem. Int. Ed. 1944, 33, 803.
14. Warnmark, K.; Thomas, J. A.; Heyke, O.; Lehn, J.-M. Chem. Commun. 1996, 701.
15. Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129.
16. Kahn, M. Synlett 1993, 821.
17. 12 These compounds are comprised of fused norbornane and bicyclo[2.2.0]hexane rings, but were not, at that time, considered as block building strategies. There, quadricyclanes served as a key reagent (a BLOCK) in the reaction of cyclobutene-1,2-diesters (another BLOCK) to yield the binane framework, which by virtue of other stereospecific cycloaddition reactions, viz Ru-catalysed addition of dimethylacetylene dicarboxylate onto norbornenes (a further BLOCK); Diels-Alder addition of cyclopentadiene (onto cyclobutene-1,2-diesters) allowed a series of rigid rods (linear systems), spacers (ones that contain a bend) and cavity molecules (the two bends were achieved using the first example of a dual BLOCK) to be produced.
18. Warrener, R. N.; Pitt, I. G.; Butler, D. N. J. Chem. Soc., Chem. Commun. 1983, 1340.
19. Klarner, F.-G.; Benkhoff, J.; Boese, R.; Burkert, U.; Kamieth, M.; Naatz, V. Angew. Chem. Int., Ed. Engl. 1996, 35, 1130.
20. Benkhoff, J.; Boese, R.; Klarner, F.-G.; Wigger, A. E. Tetrahedron Lett. 1994, 35, 73.
21. Kumar, K.; Tepper, R. J.; Zeng, Y.; Zimmt, M. B. J. Org. Chem. 1995, 60, 4051 and references therein.
22. Ashton, P. R.; Brown, G. R.; Isaacs, N. S.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Slawin, A. M. Z.; Smith, D. R.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1992, 114, 6330.
23. Ashton, P. R.; Girreser, U.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Raymo, F. M.; Slawin, A. M. Z.; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1993, 5422.
24. Mathias, J. P.; Stoddart, J. F. Chem. Soc. Rev. 1992, 21, 215.
25. Ashton, P. R.; Mathias, J. P.; Stoddart, J. F. Synthesis 1993, 221.
26. Lawson, J. M.; Oliver, A. M.; Rothenfluh, D. F.; An, Y.-Z.; Ellis, G. A.; Ranasinghe, M. G.; Khan, S. I.; Franz, A. G.; Ganapathi, P. S.; Shephard, M. J.; Paddon-Row, M. N.; Rubin, Y. J. Org. Chem. 1996, 61, 5032, and references cited therein;
27. Gulyas, P. T.; Langford, S. J.; Lokan, N. R.; Ranasinghe, M. G.; Paddon-Row, M. N. J. Org. Chem. 1997, 62, 3038.
28. Warrener, R. N.; Groundwater, P.; Pitt, I. G.; Butler, D. N.; Russell, R. A. Tetrahedron Lett. 1991, 32, 1885.
29. Warrener, R. N.; Abbenante, G.; Solomon, R. G.; Russell, R. A. Tetrahedron Lett. 1994, 35, 7639.
30. Warrener, R. N.; Maksimovic, L.; Pitt, I. G.; Mahadevan, I.; Russell, R. A.; Tiekink, E. R. T. Tetrahedron Lett. 1996, 37, 3773.
31. Warrener, R. N.; Houghton, M. A.; Schultz, A. C.; Keene, F. R.; Kelso, L. S.; Dash, R.; Butler, D. N. Chem. Commun. 1996, 1151.
32. Warrener, R. N.; Ferreira, A. B. B.; Schultz, A. C.; Butler, D. N.; Keene, F. R.; Kelso, L. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2485.
33. Warrener, R. N.; Wang, S.; Russell, R. A.; Gunter, M. J. Synlett 1997, 47.
34. Warrener, R. N.; Schultz, A. C.; Houghton, M. A.; Butler, D. N. Tetrahedron 1997, 53, 3991.
35. Warrener, R. N.; Elsey, G. M.; Sankar, I. V.; Butler, D. N.; Pekos, P.; Kennard, C. H. L. Tetrahedron Lett. 1994, 35, 6745.
36. Warrener, R. N.; Wang, S.; Butler, D. N.; Russell, R. A. Synlett 1997, 44.
37. Warrener, R. N.; Wang, S.; Russell, R. A. Tetrahedron 1997, 53, 3975.
38. Warrener, R. N.; Wang, S.; Maksimovic, L.; Tepperman, P. M.; Butler, D. N. Tetrahedron Lett. 1995, 36, 6141.
39. Butler, D. N.; Smits, R.; Evans, D. A. C.; Weerasuria, K. D. V.; Warrener, R. N. Tetrahedron Lett. 1996, 37, 2157.
40. Butler, D. N.; Tepperman, P. M.; Gau, R. A.; Warrener, R. N.; Watson, W. H.; Kashyap, R. P. Tetrahedron Lett. 1995, 36, 6145.
41. Ryan, D. E. Tetrahedron Lett. 1996, 37, 6089.
42. Performed by Dr. D. Margetic using the AM1 Hamiltonian.
43. Butler, D. N.; Malpass, J. R.; Margetic, D.; Russell, R. A.; Sun, G.; Warrener, R. N. Synlett 1998, 588.
44. Vasiliev, N. V.; Lyashenko, Y. E.; Kolomietz, A. F.; Sokolskii, G. A. Khim. Geterotsikl Soedin. 1987, 562.
45. Vasiliev, N. V.; Lyashenko, Y. E.; Patalakha, A. E.; Sokolskii, G. A. J. Fluorine Chem. 1993, 65, 227.
46. Seitz, V. G.; Wassmuth, H. Chemiker Zeitung 1988, 112, 80.
47. Seitz, G.; Gerninghaus, C. H. Pharmazie 1994, 49, 102.
48. Thalhammer, F.; Wallfahrer, U.; Sauer, J. Tetrahedron Lett. 1988, 29, 3231.
49. Warrener, R. N.; Maksimovic, L.; Elsey, G. M.; Butler, D. N. J. Chem. Soc., Chem. Commun. 1994, 1831.
50. Warrener, R. N.; Butler, D. N.; Liao, W. Y.; Pitt, I. G.; Russell, R. A. Tetrahedron Lett. 1991, 32, 1889.
51. Warrener, R. N.; Elsey, G. M.; Russell, R. A.; Pitt, I. G.; Tiekink, E. R. T. Tetrahedron Lett. 1995, 36, 5275.
52. Warrener, R. N.; Margetic, D.; Tiekink, E. R. T.; Russell, R. A. Synlett 1997, 196.
53. Warrener, R. N.; Butler, D. N. Aldrichimica Acta 1997, 30, 119.
54. Warrener, R. N.; Margetic, D.; Russell, R. A. Synlett 1998, 585.
55. Warrener, R. N. J. Am. Chem. Soc. 1971, 93, 2346.
56. Warrener, R. N.; Schultz, A. C.; Johnston, M. R.; Keene, F. R.; Kelso, L. S. 1997, unpublished results.
57. Warrener, R. N.; Johnston, M. R.; Schultz, A. C.; Golic, M.; Houghton, M. A.; Gunter, M. J. Synlett 1998, 590.
58. Warrener, R. N.; Amarasekara, A. S.; Russell, R. A., 1997, unpublished results.
59. Warrener, R. N.; Margetic, D.; Amarasekara, A. S.; Butler, D. N.; Mahadevan, I. B.; Russell, R. A., 1997, unpublished results.