Efficient Solid-Phase Synthesis of Symmetric Norbinaltorphimine Derivatives

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3807-3809

  Tanaka, Hiroshi ^a   Moriwaki, Mitsuhiro ^b   Takahashi, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TORAY INDUSTRIES INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; NORBINALTORPHIMINE;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; COMBINATORIAL CHEMISTRY; METHODOLOGY; SOLID; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0242543873     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0351854     Document Type: Article

References (22)

1. (a) Schreiber, S. L. Bioorg. Med. Chem. 1988, 6, 1127-1152.
2. (b) Stocwell, B. R.; Hardwick, J. S.; Tong, J. K.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 10662-10663.
3. Clemons, P. A. Curr. Opin. Chem. Biol. 1999, 3, 112-115.
4. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, 2002; Vols. 1 and 2.
5. For our reported solid-phase synthesis of a small-molecule library, see: (a) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 725, 3716-3722. (c) Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Tanaka, H.; Takahashi, T. Synlett 2002, 93-96. (d) Fuchi, N.; Doi, T.; Cao, B.; Kahn, M.; Takahashi, T. Synlett 2002, 285-289. (e) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (f) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 3053-3057.
6. For our reported solid-phase synthesis of a small-molecule library, see: (a) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 725, 3716-3722. (c) Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Tanaka, H.; Takahashi, T. Synlett 2002, 93-96. (d) Fuchi, N.; Doi, T.; Cao, B.; Kahn, M.; Takahashi, T. Synlett 2002, 285-289. (e) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (f) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 3053-3057.
7. For our reported solid-phase synthesis of a small-molecule library, see: (a) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 725, 3716-3722. (c) Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Tanaka, H.; Takahashi, T. Synlett 2002, 93-96. (d) Fuchi, N.; Doi, T.; Cao, B.; Kahn, M.; Takahashi, T. Synlett 2002, 285-289. (e) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (f) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 3053-3057.
8. For our reported solid-phase synthesis of a small-molecule library, see: (a) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 725, 3716-3722. (c) Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Tanaka, H.; Takahashi, T. Synlett 2002, 93-96. (d) Fuchi, N.; Doi, T.; Cao, B.; Kahn, M.; Takahashi, T. Synlett 2002, 285-289. (e) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (f) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 3053-3057.
9. For our reported solid-phase synthesis of a small-molecule library, see: (a) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 725, 3716-3722. (c) Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Tanaka, H.; Takahashi, T. Synlett 2002, 93-96. (d) Fuchi, N.; Doi, T.; Cao, B.; Kahn, M.; Takahashi, T. Synlett 2002, 285-289. (e) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (f) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 3053-3057.
10. For our reported solid-phase synthesis of a small-molecule library, see: (a) Matsuda, A.; Doi, T.; Tanaka, H.; Takahashi, T. Synlett 2001, 1101-1104. (b) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 725, 3716-3722. (c) Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Tanaka, H.; Takahashi, T. Synlett 2002, 93-96. (d) Fuchi, N.; Doi, T.; Cao, B.; Kahn, M.; Takahashi, T. Synlett 2002, 285-289. (e) Tanaka, H.; Zenkoh, T.; Setoi, H.; Takahashi, T. Synlett 2002, 1427-1430. (f) Tanaka, H.; Ohno, H.; Kawamura, K.; Ohtake, A.; Nagase, H.; Takahashi, T. Org. Lett. 2003, 5, 3053-3057.
11. For an example of intraside dimerization reaction of solid-supported substrates, see: (a) Blackwell, H. E.; Clemons, P. A.; Schreiber, S. L. Org. Lett. 2001, 3, 1185-1188. (b) Liao, Y.; Fathi, R.; Yang, Z. Org. Lett. 2003, 5, 909-912. (c) Liao, Y.; Fathi, R.; Yang, Z. J. Comb. Chem. 2003, 5, 79-81.
12. For an example of intraside dimerization reaction of solid-supported substrates, see: (a) Blackwell, H. E.; Clemons, P. A.; Schreiber, S. L. Org. Lett. 2001, 3, 1185-1188. (b) Liao, Y.; Fathi, R.; Yang, Z. Org. Lett. 2003, 5, 909-912. (c) Liao, Y.; Fathi, R.; Yang, Z. J. Comb. Chem. 2003, 5, 79-81.
13. For an example of intraside dimerization reaction of solid-supported substrates, see: (a) Blackwell, H. E.; Clemons, P. A.; Schreiber, S. L. Org. Lett. 2001, 3, 1185-1188. (b) Liao, Y.; Fathi, R.; Yang, Z. Org. Lett. 2003, 5, 909-912. (c) Liao, Y.; Fathi, R.; Yang, Z. J. Comb. Chem. 2003, 5, 79-81.
14. Portoghese, P. S.; Nagase, H.; Lipkowski, A. W.; Larson, D. L.; Takemori, A. E. J. Med. Chem. 1988, 31, 836-841.
15. (a) Portoghese P. S.; Lipkowski A. W.; Takemori A. E. J. Med. Chem. 1987, 30, 238-239.
16. (b) Portoghese P. S.; Sultana M.; Nagase H.; Takemori A. E. J. Med. Chem. 1988, 31, 281-282.
17. (a) Piloty, O. Ber. 1910, 43, 489-498.
18. (b) Robinson, G. M.; Robinson, R. J. Chem. Soc. 1918, 113, 639-645.
19. (c) Posvic, H.; Dombro, R.; Ito, H.; Telinski, T. J. Org. Chem. 1974, 39, 2575-2580.
20. Lipowski, A. W.; Nagase, H.; Portoghese, P. S. Tetrahedron Lett. 1986, 27, 4257-4260.
21. It was difficult to estimate the purity of the norBNI derivative with two secondary amino groups by reverse-phase HPLC analysis using UV absorption of 254 nm because of its high polarity.
22. 2O/0.1% HCOOH in MeCN = gradient from 95:5 (0 min) to 50:50 (10 min); UV, 254 nm.).