Synthesis of L,L-cycloisodityrosines by copper(II) acetate-DMAP-mediated intramolecular O-arylation of phenols with phenylboronic acids

Tetrahedron Letters

Volumn 44, Issue 31, 2003, Pages 5901-5903

  Hitotsuyanagi, Yukio ^a   Ishikawa, Hiroshi ^a   Naito, Syunsuke ^a   Takeya, Koichi ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; BORONIC ACID DERIVATIVE; COPPER ACETATE; ETHER DERIVATIVE; PHENOL DERIVATIVE; TYROSINE DERIVATIVE;

ARTICLE; ARYLATION; CHIRALITY; CYCLIZATION; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0037631173     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01390-X     Document Type: Article

References (32)

1. Jolad S.D., Hoffmann J.J., Torrance S.J., Wiedhopf R.M., Cole J.R., Arora S.K., Bates R.B., Gargiulo R.L., Kriek G.R. J. Am. Chem. Soc. 99:1977;8040-8044.
2. Itokawa H., Takeya K., Mihara K., Mori N., Hamanaka T., Sonobe T., Iitaka Y. Chem. Pharm. Bull. 31:1983;1424-1427.
3. Itokawa H., Takeya K., Mori N., Hamanaka T., Sonobe T., Mihara K. Chem. Pharm. Bull. 32:1984;284-290.
4. Itokawa H., Takeya K., Hitotsuyanagi Y., Morita H. Cordell G.A. The Alkaloids. 49:1997;301-387 Academic Press, New York.
5. Helynck G., Dubertret C., Frechet D., Leboul J. J. Antibiot. 51:1998;512-514.
6. Inaba T., Umezawa I., Yuasa M., Inoue T., Mihashi S., Itokawa H., Ogura K. J. Org. Chem. 52:1987;2957-2958.
7. Inoue T., Inaba T., Umezawa I., Yuasa M., Itokawa H., Ogura K., Komatsu K., Hara H., Hoshino O. Chem. Pharm. Bull. 43:1995;1325-1335.
8. Inoue T., Sasaki T., Takayanagi H., Harigaya Y., Hoshino O., Hara H., Inaba T. J. Org. Chem. 61:1996;3936-3937.
9. Boger D.L., Yohannes D. J. Am. Chem. Soc. 113:1991;1427-1429.
10. Boger D.L., Yohannes D., Zhou J., Patane M.A. J. Am. Chem. Soc. 115:1993;3420-3430.
11. Boger D.L., Patane M.A., Zhou J. J. Am. Chem. Soc. 116:1994;8544-8556.
12. Boger D.L., Zhou J. J. Am. Chem. Soc. 117:1995;7364-7378.
13. Boger D.L., Zhou J., Borzilleri R.M., Nukui S. Bioorg. Med. Chem. Lett. 6:1996;1089-1092.
14. Boger D.L., Zhou J. J. Org. Chem. 61:1996;3938-3939.
15. Boger D.L., Zhou J., Borzilleri R.M., Nukui S., Castle S.L. J. Org. Chem. 62:1997;2054-2069.
16. Krenitsky P.J., Boger D.L. Tetrahedron Lett. 43:2002;407-410.
17. Beugelmans R., Bigot A., Bois-Choussy M., Zhu J. J. Org. Chem. 61:1996;771-774.
18. Bigot A., Beugelmans R., Zhu J. Tetrahedron. 53:1997;10753-10764.
19. Bigot A., Dau M.E.T.H., Zhu J. J. Org. Chem. 64:1999;6283-6296.
20. Boisnard S., Carbonnelle A.-C., Zhu J. Org. Lett. 3:2001;2061-2064.
21. Boisnard S., Zhu J. Tetrahedron Lett. 43:2002;2577-2580.
22. Poupardin O., Ferreira F., Genet J.P., Greck C. Tetrahedron Lett. 42:2001;1523-1526.
23. Hitotsuyanagi Y., Hasuda T., Matsumoto Y., Yamaguchi K., Itokawa H., Takeya K. Chem. Commun. 2000;1633-1634.
24. Chan D.M.T., Monaco K.L., Wang R.-P., Winters M.P. Tetrahedron Lett. 39:1998;2933-2936.
25. Evans D.A., Katz J.L., West T.R. Tetrahedron Lett. 39:1998;2937-2940.
26. Lam P.Y.S., Clark C.G., Saubern S., Adams J., Winters M.P., Chan D.M.T., Combs A. Tetrahedron Lett. 39:1998;2941-2944.
27. This method of diaryl ether formation was applied to the synthesis of (S,S)-isodityrosine, but the reaction was carried out between protected 4-borono-L-phenylalanine and a L-DOPA derivative. Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977.
28. Aoyama T., Terasawa S., Sudo K., Shioiri T. Chem. Pharm. Bull. 32:1984;3759-3760.
29. Coutts S.J., Adams J., Krolikowski D., Snow R.J. Tetrahedron Lett. 35:1994;5109-5112.
30. 3) and peptide 12 (2.2 mg, 6%).
31. The epimer of 11 is less polar than 11 and more polar than peptide 12 (the data not shown). Thus, if present, the epimer of 11 should have been separated by ODS-HPLC under the conditions described in Ref. 16.
32. 3, 313 K) δ 171.68 (s), 171.14 (s), 158.15 (s), 155.85 (s), 152.90 (s), 147.20 (s), 134.38 (s), 133.40 (d), 130.15 (d), 128.02 (s), 125.63 (d), 123.41 (d), 123.37 (d), 116.32 (d), 112.60 (d), 81.06 (s), 56.28 (q), 53.52 (d), 53.23 (d), 52.53 (q), 38.51 (t), 33.07 (t), 28.29 (q).