New and improved 'LEGO' BLOCK protocols for the direct synthesis of hydrophilic ribbon molecules with acid, ester or peptide functionality

Tetrahedron Letters

Volumn 41, Issue 23, 2000, Pages 4671-4675

  Warrener, Ronald N ^a   Butler, Douglas N ^a   Margetic, Davor ^a   Pfeffer, Frederick M ^b   Russell, Richard A ^b  

^a CENTRAL QUEENSLAND UNIVERSITY   (Australia)

^b DEAKIN UNIVERSITY   (Australia)

Author keywords

Bicyclic aliphatic compounds; Cycloadditions; Epoxides; Molecular design; Peptides; Polycyclic aliphatic compounds

Indexed keywords

ACID; ALIPHATIC COMPOUND; EPOXIDE; ESTER DERIVATIVE; PEPTIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROPHILICITY; LIPOPHILICITY; REACTION ANALYSIS; SYNTHESIS;

EID: 0034640883     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00685-7     Document Type: Article

References (23)

1. (a) Schultz, A. C.; Kelso, L. S.; Johnston, M. R.; Warrener, R. N.; Keene, F. R. Inorg. Chem. 1999, 38, 4906.
2. (b) Warrener, R. N.; Schultz, A. C.; Johnston, M. R.; Gunter, M. J. J. Org. Chem. 1999, 64, 4218.
3. (c) Warrener, R. N.; Margetic, D.; Amarasekara, A. S.; Russell, R. A. Org. Lett. 1999, 1, 203.
4. (d) Warrener, R. N.; Butler, D. N.; Russell, R. A. Synlett 1998, 556.
5. (e) Warrener, R. N.; Margetic, D.; Amarasekara, A. S.; Foley, P.; Butler, D. N.; Russell, R. A. Tetrahedron Lett. 1999, 40, 4111-4114.
6. (f) Warrener, R. N.; Margetic, D.; Russell, R. A. Article 014, Electronic Conference on Heterocyclic Chemistry '98; Rzepa, H. S.; Kappe, O., Eds.; Imperial College Press, 1998 (review).
7. (g) Warrener, R. N.; Butler, D. N.; Russell, R. A. Synlett 1998, 566 (review).
8. (h) Butler, D. N.; Malpass, J. R.; Margetic, D.; Russell, R. A.; Sun, G.; Warrener, R. N. Synlett 1998, 588.
9. (i) Sun, G.; Butler, D. N.; Warrener, R. N.; Margetic, D.; Malpass, J. R. Article 062, Electronic Conference on Heterocyclic Chemistry '98; Rzepa, H. S.; Kappe, O., Eds.; Imperial College Press, 1998 (http://www.ch.ic.ac.uk/ectoc/echet98/pub/062/index.htm).
10. (j) Butler, D. N.; Hammond, M. L. A.; Johnston, M. J.; Sun, G.; Malpass, J. R.; Fawcett, J.; Warrener, R. N. Org. Lett. 2000, 2, 721-724.
11. (k) Malpass, J. R.; Butler, D. N.; Johnston, M. J.; Hammond, M. L. A.; Warrener, R. N. Org. Lett. 2000, 2, 725-728.
12. Warrener, R. N.; Schultz, A. C.; Butler, D. N.; Wang, S.; Mahadevan, I. B.; Russell, R. A. J. Chem. Soc., Chem. Commun. 1997, 1023-1024.
13. For alternative types of 'LEGO' building block techniques, see: (a) 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, 5422-5429.
14. (b) Pabst, G. R.; Sauer, J. Tetrahedron Lett. 1998, 39, 8817-8820.
15. These reactions could also be conducted under photochemical conditions (rt, benzene, 360 nm). Warrener, R. N.; Margetic, D.; Russell, R. A. 1999, unpublished.
16. All new compounds were characterised by spectroscopic data and high resolution ms. Mp (°C) and yields of a selection of new products are as follows: 10: 156-158, 51%; 11: 180-182, 13%; 14: 156-158, 43%; 18c: oil, 95%; 18d: oil, 35%; 19b: 200-202, 89%; 19c: 99-101, 50%; 19d: 177-180, 58%; 20: 223-225, 80%; 23f: oil, 76%; 24f: 112-114, 48%; 27b: oil, 67%; 28: 300, 80%; 29: 300, 66%; 31: 107-108, 84%, 32: 350, 81%.
17. 4.
18. (a) Mitsudo, T.; Kokuryo, K.; Shinsugi, T.; Nakagawa, Y.; Watanabe, Y.; Takegami, Y. J. Org. Chem. 1979, 44, 4492-4496.
19. (b) Mitsudo, T.; Naruse, H.; Kondo, T.; Ozaki, Y.; Watanabe, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 580-581.
20. (c) Warrener, R. N.; Pitt, I. G.; Butler, D. N. J. Chem. Soc., Chem. Commun. 1983, 1340-1342.
21. (d) Kumar, K.; Tepper, R. J.; Zeng, Y.; Zimmt, M. B. J. Org. Chem. 1995, 60, 4051-4066.
22. The stability of the epoxide rings in these compounds was surprising; we attribute this to the reluctance of the epoxide ring to open under acidic conditions owing to the poor stabilisation of the incipient carbocation; base stability is attributed to the inability of nucleophiles to attack from the backside of the epoxide for steric reasons.
23. 2Ph groups (we thank Professor O. DeLucchi for providing this latter sample).