Nucleophilic substitutions on Multipin™ systems linked with a traceless linker

Synlett

Volumn , Issue 11, 1998, Pages 1261-1263

  Takahashi, Takashi ^a   Tomida, Satoshi ^a   Inoue, Hitoshi ^a   Doi, Takayuki ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003136375     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1935     Document Type: Article

References (34)

1. In Combinatorial Chemistry; Wilson, S. R.; Czarnik, A. W., Eds.; John Wiley: New York, 1997.
2. Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006.
3. Hobbs DeWitt, S.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Reynolds Cody, D. M.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909.
4. Gayo, L. M.; Suto, M. J. Tetrahedron Lett. 1997, 38, 211.
5. Brown, A. R.; Rees, D. C.; Rankovic, Z.; Morphy, J. R. J. Am. Chem. Soc. 1997, 119, 3288 and references cited therein.
6. Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Nature 1997, 387, 268.
7. Pernerstorfer, J.; Schuster, M.; Blechert, S. Chem. Commun. 1997, 1949.
8. Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143 and references cited therein.
9. Hunt, J. A.; Roush, W. R., J. Am. Chem. Soc. 1996, 118, 9998.
10. Rueter, J. K.; Nortey, S. O.; Baxter, E. W.; Leo, G. C.; Reitz, A. B. Tetrahedron Lett. 1998, 39, 975.
11. Baxter, E. W.; Rueter, J. K.; Nortey, S. O.; Reitz, A. B. Tetrahedron Lett. 1998, 39, 979.
12. Zhong, H. M.; Greco, M. N.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 9326.
13. Takahashi, T.; Ebata, S.; Doi, T. Tetrahedron Lett. 1998, 39, 1369.
14. Tatsuta, K.; Fujimoto, K.; Kinoshita, M. Carbohyd. Res. 1977, 54, 85.
15. Campbell, R. W.; Hill, H. W., Jr. J. Org. Chem. 1973, 38, 1047.
16. Mitsunobu, O. Synthesis 1981, 1.
17. Hughes, D. L. Org. React. 1992, 42, 335.
18. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
19. Rink amine crowns were prepared from Fmoc-NH-Rink-Polystyrene crowns by treatment with 20% piperidine in DMF for 20 min before use. Batch no. 491-13, Loading = 2.0 μmol per crown, Chiron Technologies Pty. Ltd., 11 Duerdin St., Clayton, Victoria 3168, Australia.
20. The Multipin™ system has been successfully used in the synthesis of a chemical library. See, Valerio, R. M.; Bray, A. M.; Maeji, N. J. Int. J. Peptide Protein Res. 1994, 44, 158.
21. Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11580.
22. Valerio, R. M.; Bray, A. M.; Patsiouras, H. Tetrahedron Lett. 1996, 37, 3019.
23. Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M. J. Org. Chem. 1997, 62, 5660.
24. Complete conversion was detected by a color test (negative result) with a solution of trinitrobenzenesulfonic acid in DMF : DIEA = 10 : 1 in a few minutes.
25. After the reaction, the crowns were washed several times and treated under acid cleavage conditions to observe whether the starting material is recovered. The conversion was determined by HPLC with integration of peak area (UV, 260 nm) of the recovered material comparing with that of an authentic sample in a certain concentration.
26. Shimizu, T.; Hiranuma, S.; Nakata, T. Tetrahedron Lett. 1996, 37, 6145.
27. For intramolecular alkylation of cyanohydrin ethers: see, (a) Takahashi, T.; Nemoto, H.; Tsuji, J. Tetrahedron Lett. 1983, 24, 2005.
28. (b) Takahashi, T.; Nagashima, T.; Tsuji, J. Tetrahedron Lett. 1981, 22, 1359.
29. (c) Stork, G.; Depezay, J. C.; d'Angelo, J. Tetrahedron Lett. 1975, 389.
30. Solid phase syntheses of cyclic compounds through C-C bond formation. Wittig reaction; see: Nicolaou, K. C.; Pastor, J.; Winssinger, N.; Murphy, F. J. Am. Chem. Soc. 1998, 120, 5132.
31. Metathesis; see: Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606 and ref 6.
32. 2-Polystyrene, Batch no. 799-19, Loading = 9.3 μmol per crown. See ref 9.
33. The intramolecular alkylation of trityl protected derivative of 11 in solution phase (LiHMDS, THF, 60°C) gave the desired 10-membered ring compound 14 in 76% yield.
34. 2 for 20 min. None of the starting material was observed in HPLC analyses except Entries 8 and 9.