Synthesis of 4-Borono-L-phenylalanine

Synlett

Volumn 1996, Issue 2, 1996, Pages 167-168

  Malan, Christophe ^a   Morin, Christophe ^a  

^a UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001925040     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5344     Document Type: Article

References (33)

1. Morin, C. Tetrahedron 1994, 50, 12521.
2. Mishima, Y.; Honda, C.; Ichihashi, M.; Obara. H.; Hiratsuka, J.; Fukuda, H.; Karashima, H.; Kobayashi, T.; Kanda, K.; Yoshino, K. Lancet 1989, 388.
3. Mishima, Y.; Ichihashi, M.; Hatta, S.; Honda, C.; Yamamura, K.; Nakagawa, T. Pigm. Cell Res. 1989, 5, 226.
4. For the role of chemistry in boroneutrotherapy (BNCT), see: Hawthorne, M.F. Angew. Chem. 1993, 105, 997; Angew. Chem., Int. Ed. Engl. 1993, 32, 950.
5. For the role of chemistry in boroneutrotherapy (BNCT), see: Hawthorne, M.F. Angew. Chem. 1993, 105, 997; Angew. Chem., Int. Ed. Engl. 1993, 32, 950.
6. Snyder, H.R.; Reedy, A.J.; Lennarz, W.M.J. J. Am. Chem. Soc. 1958, 80, 835.
7. Kirihara, M.; Morimoto,; T. Ichimoto, I. Biosci. Biotech. Biochem. 1993, 57, 1940.
8. Samsel, E.G. US Patent 5157149, 1992; Chem. Abstr. 1993, 118, 125073.
9. Roberts, D.C.; Suda, K.; Samanen, J.; Kemp, D.S. Tetrahedron Lett. 1980, 21, 3435.
10. Jackson, R.F.W.; James, K.; Wythes, M.J.; Wood, A. J. Chem. Soc., Chem. Commun. 1989, 644.
11. Jackson, R.F.W.; Wishart, N.; Wood, A.; James, K.; Wythes, M.J. J. Org. Chem 1992, 57, 3397.
12. Dunn, M.J.; Jackson, R.F.W.; Pietruszka, J.; Wishart, N.; Ellis, D.; Wythes, M.J. Synlett 1993, 499.
13. Smyth, M.S.; Burke Jr. T.-R. Tetrahedron Lett. 1994, 35, 551.
14. Jackson, R.F.W.; Graham, L.J.; Rettie A.B. Tetrahedron Lett. 1994, 35, 4417.
15. Dow, R.L.; Bechle, B.M. Synlett 1994, 293.
16. For an example of a Stille coupling in the presence of a boronated moiety see: Yamamoto, Y.; Seko, T.; Nemoto, H. J. Org. Chem. 1989, 54, 4734.
17. Siebert, W.; Schaper, K.-J.; Asgarouladi, B.Z. Naturforsch. 1974, 29b, 642.
18. From 1,4-diiodobenzene (14%-19%): Bowie, R.A.; Musgrave, O.C. J. Chem. Soc. (C) 1966, 566. This yield could be raised to 40 % by use of the organolithium (C. Malan, unpublished results) but the procedure is not adaptable to large scale work.
19. 15 4-tributylstannylbenzeneboronic acid : Kinsey, B.M.; Kassis, A.M. Nucl. Med. Biol. 1993, 20, 13.
20. Model experiments carried out with benzeneboronic acid and 1,3-diphenyl-1,3-propanediol led to, after catalytic hydrogenolysis of the protected boronate, isolation of 1,3-diphenylpropane and benzeneboronic acid. No significant differences in reactivity / stability between the threo and erythro diols (prepared according to Deprés, J.-P.; Morat, C. J. Chem. Educ. 1992, 69, 232) have been found and therefore they both can be used; application of this new protecting group to other boronic acids is presently under investigation.
21. New compounds gave satisfactory elemental analyses.
22. Koehn, P.V.; Kind, C.A. Arch. Biochem. Biophys. 1965, 111, 614.
23. Baldwin, J. E.; Adlington, R.M.; Birch, D. J.; Crawford, J.A.; Sweeney, J.B. J. Chem. Soc., Chem. Commun. 1986, 1339.
24. For a general review on organozinc chemistry including activation of zinc, see : Knochel, P.; Singer, R.D. Chem. Rev. 1993, 93, 2117.
25. 2.
26. 2.
27. Tri-o-tolylphosphine is the ligand which is ususally chosen for Pd(0) coupling of organozinc 6 with aryl iodides, but other ligands active in Stille-type couplings can perform equally well; for a discussion of reactivity trends and of the importance of Pd ligands see: Farina, V.; Krishnan, B.J. Am. Chem. Soc. 1991, 113, 9585.
28. quat-CH-O); 155.1 (NHCOO-); 171.6 (C-1).
29. 4) δ : 26 (W 1/2 = 700 Hz).
30. Martin, A.R.; Yang, Y. Acta Chem. Scand. 1993, 47, 221.
31. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
32. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Tsubaki, K.; Yoshida, Z. Tetrahedron Lett. 1985, 26, 5559.
33. Due to quadrupolar relaxation, the carbon attached to boron is not detected.